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inquirymethyl 2-methoxypropanedioate Application:methyl 2-methoxypropanedioate
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inquiryPropanedioic acid,2-methoxy-, 1,3-dimethyl esterAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea, by express
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inquirychloropentamethoxycyclopropane
dimethyl methoxymalonate
Conditions | Yield |
---|---|
With silver perchlorate In methanol | 85% |
Conditions | Yield |
---|---|
dirhodium tetraacetate In dichloromethane at 18 - 20℃; for 48h; | 70% |
With dirhodium tetraacetate In dichloromethane at 20℃; for 48h; Inert atmosphere; | 70% |
With copper(l) iodide; phosphorous acid trimethyl ester | |
copper In toluene |
dimethyl methoxymalonate
Conditions | Yield |
---|---|
With sodium methylate In methanol; dichloromethane-d2 | 60% |
methanol
dimethyl diazomalonate
A
dimethyl 2-hydroxymalonate
B
dimethyl methoxymalonate
C
methyl 2-(methoxycarbonyl)-4-oxopentanonate
D
methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate
Conditions | Yield |
---|---|
In acetone for 10h; Irradiation; | A 24% B 1% C 0.5% D 31% |
dimethyl diazomalonate
acetone
A
dimethyl 2-hydroxymalonate
B
dimethyl methoxymalonate
C
methyl 2-(methoxycarbonyl)-4-oxopentanonate
D
methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate
Conditions | Yield |
---|---|
for 10h; Product distribution; Irradiation; reaction in the presence of benzophenone; | A 24% B 1% C 0.5% D 31% |
for 10h; Irradiation; | A 24% B 1% C 0.5% D 31% |
dimethyl diazomalonate
pentan-3-one
A
dimethyl 2-hydroxymalonate
B
dimethyl methoxymalonate
C
methyl 2-(methoxycarbonyl)-5-oxoheptanoate
D
methyl 2-(methoxycarbonyl)-3-oxoheptanoate
Conditions | Yield |
---|---|
for 10h; Product distribution; Irradiation; reaction in the presence of benzophenone; | A 21% B 0.6% C 3.8% D 4.7% E 13% |
dimethyl 3-methoxy-2-oxo-1,4-butanedioate
dimethyl methoxymalonate
diazomethane
dimethyl diazomalonate
dimethyl methoxymalonate
Conditions | Yield |
---|---|
(i) (irradiation), THF, H2O, (ii) /BRN= 102415/; Multistep reaction; |
diazomethane
diethyl methoxymalonate
dimethyl methoxymalonate
Conditions | Yield |
---|---|
(i) aq. NaOH, (ii) /BRN= 102415/; Multistep reaction; |
Conditions | Yield |
---|---|
With sodium methylate In benzene |
trimethylene oxide
methanol
dimethyl diazomalonate
A
dimethyl methoxymalonate
B
(3-Methoxypropoxy)malonsaeure-dimethylester
C
2-Oxetanylmalonsaeure-dimethylester
D
Tetrahydrofuran-2,2-dicarbonsaeure-dimethylester
Conditions | Yield |
---|---|
at 0℃; Irradiation; Yield given. Yields of byproduct given; |
methanol
dibenzyl 2-methoxymalonate
A
dimethyl methoxymalonate
(+)-methoxy benzyl methyl malonate
(-)-methoxy benzyl methyl malonate
Conditions | Yield |
---|---|
In hexane at 40℃; lipase from Candida cylindracea; stopped at 50percent conversion; Title compound not separated from byproducts; |
chloropentamethoxycyclopropane
A
dimethyl methoxymalonate
B
methyl 2,2,3,3-tetramethoxypropanoate
Conditions | Yield |
---|---|
With tert.-butyl lithium; oxygen 1.) ether, -78 deg C, 20 min, 2.) ether, -78 deg C, 3 h -> room temperature; Yield given. Multistep reaction. Yields of byproduct given; |
methyl methoxyacetate
carbonic acid dimethyl ester
dimethyl methoxymalonate
Conditions | Yield |
---|---|
With sodium methylate for 2h; Heating; | 18.3 g |
dimethyl methoxymalonate
Conditions | Yield |
---|---|
With silver perchlorate In methanol |
dimethyl diazomalonate
trimethyl orthoformate
A
dimethyl methoxymalonate
B
methyl 2-carbomethoxy-2,3,3-trimethoxypropanoate
Conditions | Yield |
---|---|
copper(II) bis(trifluoromethanesulfonate) at 50℃; for 4h; also with Rh2(OAc)4 as catalyst; | A 20 % Chromat. B 46 % Chromat. |
copper(II) bis(trifluoromethanesulfonate) at 50℃; for 4h; Product distribution; also with Rh2(OAc)4 as catalyst; | A 20 % Chromat. B 46 % Chromat. |
copper(II) bis(trifluoromethanesulfonate) at 50℃; for 4h; | A 20 % Chromat. B 46 % Chromat. |
methanol
dibenzyl 2-methoxymalonate
A
dimethyl methoxymalonate
C
(S)-(-)-benzyl,methyl 2-methoxymalonate
Conditions | Yield |
---|---|
In hexane at 40℃; for 0.75h; lipase from Candida cylindracea; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
Destillation; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TsN3, Et3N / acetonitrile 2: (i) (irradiation), THF, H2O, (ii) /BRN= 102415/ View Scheme | |
Multi-step reaction with 2 steps 1: TsN3, Et3N / acetonitrile 2: Cu / toluene View Scheme |
methanol
benzothiophenium bismethoxycarbonylmethylide
A
dimethyl methoxymalonate
B
malonic acid dimethyl ester
Conditions | Yield |
---|---|
In acetonitrile UV-irradiation; |
methanol
benzothiophenium bismethoxycarbonylmethylide
A
dimethyl methoxymalonate
B
malonic acid dimethyl ester
C
Benzo[b]thiophene
Conditions | Yield |
---|---|
In acetonitrile Quantum yield; UV-irradiation; |
methanol
dibenzothiophenium bismethoxycarbonylmethylide
A
dibenzothiophene
B
dimethyl methoxymalonate
C
malonic acid dimethyl ester
Conditions | Yield |
---|---|
In acetonitrile Quantum yield; UV-irradiation; |
methanol
dibenzothiophenium bismethoxycarbonylmethylide
A
dimethyl methoxymalonate
B
malonic acid dimethyl ester
Conditions | Yield |
---|---|
In acetonitrile UV-irradiation; | |
With benzophenone Inert atmosphere; UV-irradiation; | A 9 %Chromat. B 57 %Chromat. |
methanol
thiophenium bis(methoxycarbonyl)methylide
A
thiophene
B
dimethyl (2-thienyl)propanedioate
C
dimethyl methoxymalonate
D
malonic acid dimethyl ester
Conditions | Yield |
---|---|
In acetonitrile Quantum yield; UV-irradiation; |
methanol
thiophenium bis(methoxycarbonyl)methylide
A
dimethyl (2-thienyl)propanedioate
B
dimethyl methoxymalonate
C
malonic acid dimethyl ester
Conditions | Yield |
---|---|
In acetonitrile UV-irradiation; |
Conditions | Yield |
---|---|
at 80℃; Inert atmosphere; |
methanol
C9H8Br2O4S
A
dimethyl methoxymalonate
B
malonic acid dimethyl ester
Conditions | Yield |
---|---|
Inert atmosphere; UV-irradiation; | A 86.5 %Chromat. B 9.4 %Chromat. |
methanol
dimethylmalonate-3,4-dibromothiophene-S,C-ylide
dimethyl methoxymalonate
Conditions | Yield |
---|---|
at 80℃; Inert atmosphere; |
dimethyl methoxymalonate
methoxymalonic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide at 65℃; | 100% |
With potassium hydroxide In methanol Heating; | 1.28 g |
2-bromo-5-bromomethylpyridine
dimethyl methoxymalonate
dimethyl [(6-bromopyridin-3-yl)methyl](methoxy)malonate
Conditions | Yield |
---|---|
With potassium tert-butylate In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 3.5h; | 100% |
dimethyl methoxymalonate
diguanidine carbonate
2-amino-5-methoxypyrimidine-4,6-diol
Conditions | Yield |
---|---|
Stage #1: diguanidine carbonate With ethanol; sodium at 80℃; for 0.5h; Inert atmosphere; Stage #2: dimethyl methoxymalonate at 80℃; for 2h; | 100% |
dimethyl methoxymalonate
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃; for 1h; | 99% |
dimethyl methoxymalonate
sodium methylate
urea
6-hydroxy-5-methoxy-1H-pyrimidine-2,4-dione
Conditions | Yield |
---|---|
Stage #1: dimethyl methoxymalonate; sodium methylate; urea In ethanol at 100℃; for 4h; Stage #2: With hydrogenchloride In ethanol; water pH=3 - 4; | 99% |
formaldehyd
dimethyl methoxymalonate
dimethyl 2-(hydroxymethyl)-2-methoxymalonate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol; water at 0 - 20℃; for 20h; | 98% |
With sodium hydrogencarbonate In ethanol; water at 0 - 20℃; for 20h; | 98% |
bis(1,1-dimethylethyl) [[(8-aminooctyl)imino]methylene]biscarbamate
dimethyl methoxymalonate
A
1-(1,1-Dimethylethyl) 16-methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-15-methoxy-14-oxo-2,4,13-triazahexadec-2-enedioate
B
1-(1,1-Dimethylethyl) 16-ethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-15-phenylmethoxy-14-oxo-2,4,13-triazahexadec-2-enedioate
Conditions | Yield |
---|---|
A 95% B n/a |
dimethyl methoxymalonate
(4-methoxyphenyl)methyl methyl carbonate
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 24h; | 94% |
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,5-cis,cis-cyclooctadiene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃; | 90% |
With 1,1'-bis(diisopropylphosphino)ferrocene; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; caesium carbonate In N,N-dimethyl-formamide at 30℃; for 24h; Inert atmosphere; | 90% |
dimethyl methoxymalonate
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 24h; | 92% |
dimethyl methoxymalonate
Di-tert-butyl acetylenedicarboxylate
triphenylphosphine
Conditions | Yield |
---|---|
In toluene for 5h; Heating; | 92% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 120℃; for 6h; Inert atmosphere; Cooling with ice; | 91.67% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 16h; Cooling with ice; Inert atmosphere; | 91.67% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Cooling with ice; | 91.67% |
dimethyl methoxymalonate
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide at 20℃; Inert atmosphere; | 91% |
dimethyl methoxymalonate
dimethyl acetylenedicarboxylate
triphenylphosphine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; | 90% |
dimethyl methoxymalonate
benzyl methyl carbonate
dimethyl O-methylbenzyltartronate
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 48h; | 88% |
dimethyl methoxymalonate
(4-hydroxyphenyl)methanol
2-(4-hydroxy-benzyl)-2-methoxy-malonic acid dimethyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 3h; Heating / reflux; | 88% |
2-(6-aminohexyl)-1,3-diBocguanidine
dimethyl methoxymalonate
A
1-(1,1-Dimethylethyl) 14-methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-13-methoxy-12-oxo-2,4,11-triazatetradec-2-enedioate
B
3-<<(1,1-dimethylethoxy)carbonyl>amino>-20-<(1,1-dimethylethoxy)carbonyl>-12,14-dioxo-2,4,11,15,20,24-hexaazapentacosenedioic acid, bis(1,1-dimethylethyl)ester
Conditions | Yield |
---|---|
A n/a B 87% |
dimethyl methoxymalonate
dimethyl 2-fluoro-2-methoxymalonate
Conditions | Yield |
---|---|
With sodium hydride; Selectfluor In tetrahydrofuran for 0.333333h; Ambient temperature; | 86% |
With sodium hydride; fluorine In acetonitrile 1.) r.t., 1 h, 2.) -15 deg C, 1 h; | 51 % Spectr. |
dimethyl methoxymalonate
diphenylmethyl methyl carbonate
Conditions | Yield |
---|---|
With sodium carbonate; [Pd(ϖ-C3H5)(cod)]BF4 In N,N-dimethyl-formamide at 120℃; for 24h; | 86% |
dimethyl methoxymalonate
propargyl bromide
dimethyl 2-methoxy-2-(2-propynyl)malonate
Conditions | Yield |
---|---|
Stage #1: dimethyl methoxymalonate With n-butyllithium In hexane; tert-butyl alcohol for 0.25h; Stage #2: propargyl bromide In hexane; toluene; tert-butyl alcohol at 20℃; for 20h; | 84% |
dimethyl methoxymalonate
benzyl alcohol
(S)-(-)-benzyl,methyl 2-methoxymalonate
Conditions | Yield |
---|---|
In hexane at 40℃; for 3.5h; lipase from Candida cylindracea; | 83% |
dimethyl methoxymalonate
[(4-trifluoromethyl)phenyl]methyl methyl carbonate
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 48h; | 83% |
dimethyl methoxymalonate
tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 30℃; for 24h; | 83% |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium carbonate; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4 In tert-Amyl alcohol at 80℃; for 48h; | 83% |
dimethyl methoxymalonate
Fe(CO)2(P(C6H5)3)(C5H6CH3)(1+)*PF6(1-)=[Fe(CO)2(P(C6H5)3)(C5H6CH3)]PF6
Conditions | Yield |
---|---|
With LDA In tetrahydrofuran stirring dimethyl methoxymalonate with LDAi at -78°C, addn. of Fe-complex, warming to 0°C, stirring for 2.5 h; addn. of H2O, extn. into ether, drying of org. layer (MgSO4), evapn., chromy. (SiO2, hexanes/EtOAc=15:1); elem. anal.; | A 83% B 9% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; | 82% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; | 82% |
Conditions | Yield |
---|---|
With indium(III) chloride at 140℃; | 81% |
dimethyl methoxymalonate
triphenylphosphine
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; | 81% |
3-[3-(benzyloxy)phenylthio]-6-vinyl-1-chlorobenzene
dimethyl methoxymalonate
2-(2-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}ethyl)-2-methoxymalonic acid dimethyl ester
Conditions | Yield |
---|---|
Stage #1: dimethyl methoxymalonate With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 3-[3-(benzyloxy)phenylthio]-6-vinyl-1-chlorobenzene In dimethyl sulfoxide at 20 - 35℃; Further stages.; | 79% |
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