diazomethane
(R)-3-hydroxybutyric acid
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
In diethyl ether | 100% |
In methanol; diethyl ether at -10℃; | 76% |
acetoacetic acid methyl ester
A
(S)-3-hydroxybutyric acid methyl ester
B
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With Ru2Cl4-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt3; hydrogen In methanol at 35℃; under 76000.1 Torr; for 48h; Title compound not separated from byproducts; | A 100% B n/a |
With <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; hydrogen In methanol at 35℃; under 76000.1 Torr; for 48h; Title compound not separated from byproducts; | A n/a B 100% |
With hydrogen; Ru(BICP)Br2 In methanol at 40 - 65℃; under 750.075 - 3750.38 Torr; | A n/a B 95% |
Conditions | Yield |
---|---|
With cat; hydrogen In methanol; dichloromethane at 25℃; under 77572.2 Torr; for 48h; | 100% |
With (R)-MeOBiphepRuBr2; hydrogen In methanol at 50℃; under 15200 Torr; for 48h; | 100% |
With (S)-4,12-bis(diphenylphosphino)-<2.2>paracyclophane-Ru(II)bis(trifluoroacetate); hydrogen; tetra-(n-butyl)ammonium iodide In methanol; water at -5℃; under 2585.7 Torr; for 18h; | 100% |
Conditions | Yield |
---|---|
scandium tris(trifluoromethanesulfonate) at 64℃; for 10h; | 98% |
(EtO)3TiO(CH2)2OTi(OEt)3 autoclave, 1.) 160 deg C, 17 bar, 2 h; 2.) 115 deg C, 3.5 bar, 27 h; | 82% |
tert-butyl acetoacetate
A
Methyl (R)-3-hydroxybutyrate
B
tert-butyl (R)-3-hydroxybutanoate
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; [RuCl2-((R)-binap)]*NEt3 In methanol at 40℃; under 2585.7 Torr; for 8h; Kinetics; effect of acid, other substrate; | A 3% B 97% |
With hydrogenchloride; hydrogen; <(R)-(BINAP)RuCl2>2*NEt3 In methanol at 40℃; under 2585.7 Torr; for 8h; | A 3% B 97% |
acetoacetic acid methyl ester
A
(S)-3-hydroxybutyric acid methyl ester
B
Methyl (R)-3-hydroxybutyrate
C
3,3-bismethoxybutyric acid methyl ester
Conditions | Yield |
---|---|
With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I In methanol at 30℃; under 76000 Torr; for 35h; Product distribution; other: catalysts, solvents, time, pressure, temperatures; | A 97% B n/a C 3% |
methanol
carbon monoxide
(R)-propylene oxide
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With 3-HYDROXYPYRIDINE; dicobalt octacarbonyl In tetrahydrofuran at 65℃; under 31028.9 Torr; for 9h; | 92% |
(S)-3-Hydroxy-4-((R)-toluene-4-sulfinyl)-butyric acid methyl ester
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With nickel | 90% |
methanol
A
methyl (3R)-3-hydroxypentanoate
B
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With sulfuric acid In 1,2-dichloro-ethane for 48h; Heating; | A 62% B 87% |
Methyl (S)-4-(p-Chlorophenylthio)-3-hydroxybutanoate
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
nickel | 80% |
Conditions | Yield |
---|---|
With sulfuric acid In dichloromethane for 48h; Heating; | 78% |
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With nickel In ethanol for 0.5h; Ambient temperature; | 75% |
Conditions | Yield |
---|---|
With sulfuric acid In 1,2-dichloro-ethane at 80℃; for 120h; Heating / reflux; | 73% |
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With sulfuric acid In methanol; 1,2-dichloro-ethane for 72h; depolymerization; Heating; | 71% |
(R)-methyl 3-(dimethyl(phenyl)silyl)butanoate
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With peracetic acid; palladium diacetate; mercury(II) diacetate In acetic acid for 2h; Ambient temperature; | 43% |
diazomethane
3-Hydroxybutyric acid
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
In diethyl ether |
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With Raney Ni W-4 Yield given; |
(R)-3-(benzyloxy)butanoic acid methyl ester
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In acetic acid Product distribution; Ambient temperature; |
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
With sulfuric acid 1.) 1,2-dichloroethane, reflux, 2 h; 2.) reflux, 48 h; Yield given. Multistep reaction; |
methanol
A
methyl (3R)-3-hydroxypentanoate
B
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With sulfuric acid 1.) 1,2-dichloroethane, reflux, 1 h; 2.) 1,2-dichloroethane, reflux, 3 d; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With sulfuric acid; toluene-4-sulfonic acid 1.) 1,2-dichloroethane, reflux, 34 h; 2.) 1,2-dichloroethane, reflux, 12 h; Yield given; Multistep reaction; |
diazomethane
(+)-macrosphelide E
A
Methyl (R)-3-hydroxybutyrate
B
methyl (E,4R,5S)-4,5-dihydroxy-2-hexenoate
Conditions | Yield |
---|---|
Stage #1: (+)-macrosphelide E With potassium carbonate In methanol at 20℃; Stage #2: diazomethane In diethyl ether at 20℃; for 2h; Further stages.; |
methanol
(+)-macrosphelide E
A
Methyl (R)-3-hydroxybutyrate
B
methyl (E,4R,5S)-4,5-dihydroxy-2-hexenoate
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; Title compound not separated from byproducts.; |
3-hydroxybutyric acid methyl ester
A
(S)-3-hydroxybutyric acid methyl ester
B
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With air; cells of Geotrichum candidum IFO5767 In water at 30℃; for 24h; Product distribution; | |
With pentyl cage-coated capillary column Resolution of racemate; | |
With homochiral metal-organic cage [Zn3(deprotonated [3+3] macrocyclic Schiff base of trans-1,2-diaminocyclohexane and 4-tert-butyl-2,6-diformylphenol)2] coated capillary column In dichloromethane at 112℃; Resolution of racemate; enantioselective reaction; |
acetoacetic acid methyl ester
isopropyl alcohol
A
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With hydrogen; (S)-Ru-BINAP at 60℃; under 30002.4 Torr; for 1h; Product distribution; Further Variations:; Reagents; Solvents; |
(R)-3-hydroxybutyric acid
diazomethyl-trimethyl-silane
Methyl (R)-3-hydroxybutyrate
Methyl 4-(4-Chlorophenylthio)-3-oxobutanoate
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Candida guilliermondii 2: 80 percent / Raney nickel View Scheme |
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / Et3N / tetrahydrofuran / 1 h / 0 °C 2: 75 percent / Raney nickel / ethanol / 0.5 h / Ambient temperature View Scheme |
triisopropylsilyl trifluoromethanesulfonate
Methyl (R)-3-hydroxybutyrate
methyl 3(R)-<oxy>butanoate
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine for 3h; Ambient temperature; | 100% |
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; | 95% |
Methyl (R)-3-hydroxybutyrate
tert-butyldimethylsilyl chloride
methyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 23℃; for 12h; Addition; | 100% |
With 1H-imidazole In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; | 100% |
With 1H-imidazole In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; | 100% |
(R)-methoxytrifluoromethylphenylacetyl chloride
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With pyridine In tetrachloromethane for 12h; Ambient temperature; | 100% |
Methyl (R)-3-hydroxybutyrate
(S)-chlorofluoroacetic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Esterification; | 100% |
{ONOMe,Cumyl}Y[N(SiHMe2)2](THF)(Et2O)
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
In benzene-d6 for 0.166667h; Inert atmosphere; Glovebox; | 99% |
Methyl (R)-3-hydroxybutyrate
benzylamine
(R)-N-benzyl-3-hydroxybutanamide
Conditions | Yield |
---|---|
With ammonium nitrate In neat (no solvent) at 20℃; for 12h; Green chemistry; | 99% |
Methyl (R)-3-hydroxybutyrate
ethyl vinyl ether
methyl (1'RS,3R)-3-(1-ethoxyethoxy)butyrate
Conditions | Yield |
---|---|
With trifluoroacetic acid for 12h; Ambient temperature; | 98% |
With trifluoroacetic acid 1) 0 deg C, 22 h, 2) r.t., 3 h; | 94% |
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 24h; |
Methyl (R)-3-hydroxybutyrate
p-toluenesulfonyl chloride
methyl (R)-3-(p-toluenesulfonyloxy)butyrate
Conditions | Yield |
---|---|
With pyridine at 0℃; for 24h; | 98% |
With pyridine; triethylamine In toluene at 0 - 20℃; Inert atmosphere; | 84% |
With pyridine Ambient temperature; | 82.4% |
2-Methoxyethoxymethyl chloride
Methyl (R)-3-hydroxybutyrate
(R)-3-(2-Methoxy-ethoxymethoxy)-butyric acid methyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane Ambient temperature; | 98% |
Methyl (R)-3-hydroxybutyrate
chloromethyl methyl ether
(R)-methyl 3-(methoxy)methoxybutyrate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine | 97% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 42h; | 95% |
With N-ethyl-N,N-diisopropylamine In dichloromethane | |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 42h; Ambient temperature; |
Methyl (R)-3-hydroxybutyrate
tert-butylchlorodiphenylsilane
(R)-3-(tert-Butyldiphenylsilanyloxy)butyric acid methyl ester
Conditions | Yield |
---|---|
Stage #1: Methyl (R)-3-hydroxybutyrate With 1H-imidazole In dichloromethane at 0℃; for 0.166667h; Stage #2: tert-butylchlorodiphenylsilane In dichloromethane at 25℃; for 4h; Further stages.; | 97% |
Stage #1: Methyl (R)-3-hydroxybutyrate With 1H-imidazole In dichloromethane at 0℃; for 0.166667h; silylation; Stage #2: tert-butylchlorodiphenylsilane In dichloromethane at 0 - 25℃; for 4h; silylation; Further stages.; | 97% |
With 1H-imidazole In dichloromethane at 20℃; for 4.5h; | 91.2% |
3,4-dihydro-2H-pyran
Methyl (R)-3-hydroxybutyrate
methyl (R)-3-tetrahydropyranyloxybutanoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 2h; Etherification; | 96% |
With toluene-4-sulfonic acid In diethyl ether for 10h; Ambient temperature; | 91% |
With toluene-4-sulfonic acid In diethyl ether at 0 - 25℃; | 65% |
chlorodimethyl(1,1,2-trimethylpropyl)silane
Methyl (R)-3-hydroxybutyrate
(R)-3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-butyric acid methyl ester
Conditions | Yield |
---|---|
96% |
Conditions | Yield |
---|---|
With 4-vinylpyridine In dichloromethane at 20℃; for 6h; | 96% |
Methyl (R)-3-hydroxybutyrate
O-(4-methoxybenzyl)-trichloroacetimidate
(R)-methyl 3-((4-methoxybenzyl)oxy)butanoate
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In dichloromethane at 20℃; for 36h; Etherification; | 95% |
With camphorsulfonic acid In dichloromethane at 20℃; Inert atmosphere; | 94% |
With camphor-10-sulfonic acid In dichloromethane at 20℃; Inert atmosphere; | 93.7% |
Conditions | Yield |
---|---|
In 2-methyltetrahydrofuran at 90℃; for 3h; Solvent; Temperature; Large scale; | 95% |
In dichloromethane at 90℃; for 4h; Solvent; Temperature; Large scale; |
Conditions | Yield |
---|---|
Stage #1: Methyl (R)-3-hydroxybutyrate With potassium hydroxide In water at 0 - 20℃; for 48h; Inert atmosphere; Stage #2: With hydrogenchloride In water pH=1; Inert atmosphere; | 94% |
With potassium hydroxide In water at 4℃; for 480h; | 91% |
Stage #1: Methyl (R)-3-hydroxybutyrate With potassium hydroxide; water at 0℃; for 25.5h; Stage #2: With hydrogenchloride; water at 5℃; | 87% |
Methyl (R)-3-hydroxybutyrate
aniline
A
methyl (R)-3-(phenylamino)butanoate
B
(S)-phenylamino-butyric acid methyl ester
Conditions | Yield |
---|---|
Stage #1: Methyl (R)-3-hydroxybutyrate With trifluoromethanesulfonic acid anhydride; diisopropylamine In dichloromethane at -78℃; for 1h; Stage #2: aniline at -78 - -40℃; for 16h; | A n/a B 94% |
Methyl (R)-3-hydroxybutyrate
benzyl bromide
(R)-3-(benzyloxy)butanoic acid methyl ester
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere; | 94% |
Methyl (R)-3-hydroxybutyrate
O-(4-methoxybenzyl)-trichloroacetimidate
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In dichloromethane at 0 - 20℃; | 94% |
Methyl (R)-3-hydroxybutyrate
sodium (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol at 15℃; for 12h; Inert atmosphere; | 93.69% |
With sodium hydroxide In water at 10 - 30℃; for 6h; | 85% |
chloro-trimethyl-silane
Methyl (R)-3-hydroxybutyrate
methyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 23h; | 92% |
Methyl (R)-3-hydroxybutyrate
Conditions | Yield |
---|---|
With calcium hydroxide In water at 8℃; for 6h; | 91.1% |
Molecular Structure of Methyl (R)-(-)-3-hydroxybutyrate (CAS NO.3976-69-0):
IUPAC Name: Methyl (3R)-3-hydroxybutanoate
Molecular Formula: C5H10O3
Molecular Weight: 118.13
EINECS: 223-610-0
XLogP3-AA: -0.2
H-Bond Donor: 1
H-Bond Acceptor: 3
Storage temp.: 0-6 °C
Index of Refraction: 1.42
Molar Refractivity: 28.48 cm3
Molar Volume: 112.4 cm3
Surface Tension: 33.2 dyne/cm
Density: 1.05 g/cm3
Flash Point: 71.7 °C
Enthalpy of Vaporization: 46.4 kJ/mol
Boiling Point: 161.9 °C at 760 mmHg
Vapour Pressure: 0.768 mmHg at 25 °C
Appearance: clear colorless liquid
Canonical SMILES: CC(CC(=O)OC)O
Isomeric SMILES: C[C@H](CC(=O)OC)O
InChI: InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1
InChIKey: LDLDJEAVRNAEBW-SCSAIBSYSA-N
Product Categories: Alcohols, Hydroxy Esters and Derivatives; Chiral Compounds; Building Blocks for Liquid Crystals; Chiral Building Blocks; Chiral Compounds (Building Blocks for Liquid Crystals); Functional Materials; Simple Alcohols (Chiral); Synthetic Organic Chemistry; Chiral Building Blocks; Esters; Organic Building Blocks; Chiral Alcohols
Safety Information of Methyl (R)-(-)-3-hydroxybutyrate (CAS NO.3976-69-0):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37-24/25-23
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S24/25:Avoid contact with skin and eyes.
S23:Do not breathe vapour.
WGK Germany: 3
Methyl (R)-(-)-3-hydroxybutyrate (CAS NO.3976-69-0), its Synonyms are (R)-(-)-3-Hydroxybutyric acid methyl ester ; Methyl (3R)-3-hydroxybutanoate ; Methyl R-3-hydroxybutanoate ; Methyl 3-hydroxybutanoate .
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View