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ETHANOL-D
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ethoxy(diphenyl)-λ6-sulfanenitrile
A
ethyl [2]alcohol
B
S,S-diphenylsulphoximine
Conditions | Yield |
---|---|
With [D3]acetonitrile; water-d2 In phosphate buffer at 20℃; for 0.75h; pH=6.1; Kinetics; Thermodynamic data; Product distribution; Further Variations:; pH-values; Reagents; Solvents; Temperatures; Hydrolysis; | A 86% B 99% |
Conditions | Yield |
---|---|
With triphenyl phosphine In benzene-d6; (2)H8-toluene (N2); dissolved Ir-compound with 1 drop toluene-d-8; placed in NMR tube; added triphenyl phosphine; (2)H NMR; | A n/a B 64% |
Conditions | Yield |
---|---|
With sulfuric acid; water-d2 |
Conditions | Yield |
---|---|
With (CD3COCD3)D(1+) In gas at 57.9℃; Rate constant; Mechanism; Thermodynamic data; experiment conditions: NBS pulsed ion cyclotron resonance; probability of a reactive H/D exchange encounter for the deuteronated ion as a function of the Gibbs free-energy change of the (endoergic) deuteron transfer reaction; | |
With (C2D5)2OD(1+) In gas at 57.9℃; Rate constant; Mechanism; experiment conditions: NBS pulsed ion cyclotron resonance; probability of a reactive H/D exchange encounter for the deuteronated ion as a function of the Gibbs free-energy change of the (endoergic) deuteron transfer reaction; | |
With water-d2 In water at 34.9℃; Equilibrium constant; |
Conditions | Yield |
---|---|
With sulfuric acid; water-d2 |
Conditions | Yield |
---|---|
With water-d2; decalin | |
With diethyl ether; water-d2 | |
With water-d2 |
Conditions | Yield |
---|---|
With decane; water-d2 | |
With water-d2 at 80℃; |
Conditions | Yield |
---|---|
With thionyl chloride; water-d2 1.) 0 deg C, 1 h, 2.) ambient temp., 2 h, 3) reflux, 4 weeks; | 175 g |
methylene chloride
diazomethane-d2
A
ethanol
B
chloromethane-d2
C
ethyl [2]alcohol
D
D3-chloromethane
Conditions | Yield |
---|---|
at -78℃; Product distribution; Irradiation; various alkylhalides; |
chloroform-d1
diethoxyltriphenylphosphorane
A
chloroethane
B
ethyl [2]alcohol
C
ethyl deuterioformate
D
Triphenylphosphine oxide
Conditions | Yield |
---|---|
at 70℃; for 72h; | |
at 70℃; for 72h; Product distribution; |
Conditions | Yield |
---|---|
Equilibrium constant; |
ethane
A
ethylene glycol-d2
B
ethyl [2]alcohol
C
deuteroacetic acid
D
(O-2H2)-glycolic acid
Conditions | Yield |
---|---|
With potassium tetrachloroplatinate; water-d2; oxygen; platinum at 108℃; under 25857.4 Torr; for 19h; Product distribution; Mechanism; var. temperatures and reaction time; | A 0.002 mmol B 0.004 mmol C 0.002 mmol D 0.0017 mmol |
carbon monoxide
orthoformic acid triethyl ester
A
diethyl ether
B
ethyl [2]alcohol
Conditions | Yield |
---|---|
With deuterium; Λ(+)-tris(pentane-2,5-dionato)ruthenium; methyl iodide Product distribution; 1.) 150 deg C, 4 h, 14 MPa, CO/D2=2.5; 2.) 170 deg C, 4 h, 10 MPa, CO/D2=2.5; 3.) 200 deg C, 6 h, 8 MPa, CO/D2=1.0; product distribution after successive steps; | A n/a B n/a C 7.0 % Chromat. D 3.0 % Chromat. E 1.0 % Chromat. F 0.3 % Chromat. |
Conditions | Yield |
---|---|
at 18℃; Kinetics; Equilibrium constant; |
d(4)-methanol
acetyl propionyl peroxide
A
methane
B
Monodeuteromethan
C
ethyl [2]alcohol
Conditions | Yield |
---|---|
at 39.85℃; for 0.666667h; Product distribution; Further Variations:; Temperatures; reaction times; |
acetyl propionyl peroxide
A
methane
B
Monodeuteromethan
C
ethyl [2]alcohol
D
n-butane
Conditions | Yield |
---|---|
With d(4)-methanol at -60.15℃; for 2h; Product distribution; Further Variations:; Temperatures; reaction times; |
acetic acid tert-butyl ester
d(4)-methanol
A
ethyl [2]alcohol
B
tert-butyl alcohol-d
Conditions | Yield |
---|---|
With sodium methylate; lanthanum(lll) triflate at 25℃; pH=8; Kinetics; |
d(4)-methanol
ethyl acetate
A
ethyl [2]alcohol
B
methyl acetate-d3
Conditions | Yield |
---|---|
With sodium methylate; lanthanum(lll) triflate at 25℃; pH=8.5; Kinetics; Further Variations:; Reagents; | |
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; | |
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; |
ammonium 3,5-dicyano-4-ethyl-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridin-2-olate
A
ethane
B
ethyl [2]alcohol
C
2,6-dihydroxy-4-methyl-pyridine-3,5-dicarbonitril; ammonium salt
Conditions | Yield |
---|---|
With borax; diclazuril In water-d2 at 20℃; pH=8; |
ethyl [2]alcohol
Conditions | Yield |
---|---|
With sodium periodate In water-d2; [D3]acetonitrile at 100℃; for 14h; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; |
d(4)-methanol
ethyl N-isobutyryl-N-methylglycinate
A
ethyl [2]alcohol
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis; |
ethyl [2]alcohol
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; | 100% |
ethyl [2]alcohol
Conditions | Yield |
---|---|
With n-C4H9Li In tetrahydrofuran (Ar, Schlenk tube technique); n-BuLi is added to a THF soln. of the complex cooled to -78°C, the mixture is stirred for 70 min, EtOD is added, the mixture is warmed up to room temp.; the volatiles are removed under reduced pressure, the products are extd. with ether and filtered through an alumina pad, product is detected by (1)H-NMR; | 99% |
With NaOC2H5 In tetrahydrofuran byproducts: (Fe(C5Me5)(CO)2)2; Irradiation (UV/VIS); (Ar, Schlenk tube technique); EtONa-EtOD is added to a THF soln. of the complex, the mixture is stirred for 2 h at ambient temp.; the volatiles are removed under reduced pressure, the products are extd. with ether and filtered through an alumina pad, product is detected by (1)H-NMR; | 99% |
hydrogen cation In ethyl [2]alcohol |
Conditions | Yield |
---|---|
With hydrogenchloride at 0℃; | 95% |
ethyl [2]alcohol
(C5(CH3)5)Rh(P(CH3)3)((13)CHCH2CH2)I
(C5(CH3)5)Rh(P(CH3)3)((13)CHCH2CH2)(H)
Conditions | Yield |
---|---|
With tert.-butyl lithium In not given (N2); -78°C; deuteration with C2H5OD at -60°C; 55% 13C-enriched according to NMR; | 93% |
ethyl [2]alcohol
5-Azidocarbonyloxy-7-phenyl-2,2-dimethyl-3-heptyne
C18H24(2)HNO3
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; iron(II) chloride at 20℃; Cyclization; Intramolecular amination; | 91% |
ethyl [2]alcohol
bromoacetic-2,2-d2 acid bromoanhydride
ethyl bromo-<2,2-2H2>acetate
Conditions | Yield |
---|---|
Ambient temperature; | 90% |
Conditions | Yield |
---|---|
With potassium In tetrahydrofuran byproducts: CH3CH2OH; mixture of ferrocenyl-compd. and EtOD in THF or pure EtOD, in which metallic K was dissolved, was stirred in absence of O2 and moisture at 50°C during 4 h, stored for 12 h at 25°C; removing of the solvent in vacuum, extn. of the residue with abs. ether, filtn. and evapn., chromatographed on a thin layer of silica gel; | 90% |
ethyl [2]alcohol
Conditions | Yield |
---|---|
With potassium In tetrahydrofuran byproducts: CH3CH2OH; mixture of EtOD and ferrocenyl-compd. in THF or pure EtOD, in which metallic K was dissolved, was stirred in absence of O2 and moisture at 50°C during 4 h, stored for 12 h at 25°C; removing of the solvent in vacuum, extn. of the residue with abs. ether, filtn. and evapn., chromatographed on a thin layer of silica gel; | 90% |
pentamethylcyclopentadienyliridium(III) PMe3 dihydride
ethyl [2]alcohol
Conditions | Yield |
---|---|
With silica gel In ethyl [2]alcohol N2-atmosphere; degassed EtOD; stirring (16 h, room temp.); evapn. (vac.); EtOD addn.; stirring (16 h, room temp.); evapn. (vac.); suspended in pentane; filtration (Celite); evapn. (vac.);isotopic purity detd. by (1)H NMR spectroscopy; | 90% |
ethyl [2]alcohol
2-bromoacetic-d2 acid-d
ethyl bromo-<2,2-2H2>acetate
Conditions | Yield |
---|---|
With sulfuric acid In benzene for 4.5h; Heating; | 89% |
Conditions | Yield |
---|---|
In dichloromethane (Ar, Schlenk tube technique); EtOD and CF3COOH are added to a CH2Cl2 soln. of the complex, the mixture is stirred for 30 min at room temp.; the volatiles are evapd., the products are extd. with ether and filtered through an alumina pad, solvent is removed; | 89% |
Conditions | Yield |
---|---|
In diethyl ether at 5℃; for 1.5h; Irradiation; | 84% |
3,5-dichloro-pyrazine-2-carboxylic acid methyl ester
ethyl [2]alcohol
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; potassium carbonate; deuterium at 20℃; under 6000.6 Torr; for 1h; Sealed tube; | 83% |
ethyl [2]alcohol
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 50℃; for 4.5h; | 81.3% |
ethyl [2]alcohol
6-chloro-pyrazine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; potassium carbonate; deuterium at 20℃; under 6000.6 Torr; for 1h; Sealed tube; | 79% |
2,5-dichloroisonicotinic acid methyl ester
ethyl [2]alcohol
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; potassium carbonate; deuterium at 20℃; under 6000.6 Torr; for 4h; Sealed tube; | 72% |
With palladium on activated charcoal; potassium carbonate; deuterium |
(CH3)3Ge(B(C4H9)2)CCH(OC2H5)
ethyl [2]alcohol
(CH3)3Ge((2)H)CC(H)OC2H5
Conditions | Yield |
---|---|
In tetrahydrofuran under Ar; dropwise addn. of soln. of alcohol to the ether; fractionated; elem. anal.; | 70% |
Conditions | Yield |
---|---|
[Cp*RuCl(η2-SMe)]2 at 20℃; for 4h; | 67% |
Conditions | Yield |
---|---|
In ethyl [2]alcohol 48 h at r.t.; filtered, washed (EtOH/H2O 1:1 then H2O), dried (80°C, 72 h, 0.01 Torr); | 66% |
ethyl [2]alcohol
methyl 5-chloropyrazine-2-carboxylate
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; potassium carbonate; deuterium at 20℃; under 6000.6 Torr; for 1h; Sealed tube; | 65% |
ethyl [2]alcohol
Conditions | Yield |
---|---|
In diethyl ether under argon, addn. of Al-compound to a stirred suspn. of Ru-complex at -78°C, slow warming to room temperature, stirring for 5 h, cooling again to -78°C, addn. of EtOD, warming to room temperature, stirring for 12 h; removing solvent (reduced pressure), extn. of residue (toluene), filtn., concg. filtrate, chromy. (alumina); | 63% |
ethyl [2]alcohol
Conditions | Yield |
---|---|
With cyanocobalamin | 60% |
ethyl [2]alcohol
Conditions | Yield |
---|---|
With LiAlH4 In diethyl ether under argon, addn. of Al-compound to a stirred suspn. of Ru-complex at -78°C, slow warming to room temperature, stirring for 5 h, cooling again to -78°C, addn. of EtOD, warming to room temperature, stirring for 12 h; removing solvent (reduced pressure), extn. of residue (toluene), filtn., concg. filtrate, chromy. (alumina); | 60% |
ethyl [2]alcohol
4-methyliminomethyl-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl
[(C3N2)(CH3)4(O)(CH(OCH2CH3)N(2)H(CH3))]CuCl2
Conditions | Yield |
---|---|
In ethyl [2]alcohol for 1-24 h; ppt. filtered off, washed (ethanol-d); elem. anal.; | 60% |
ethyl [2]alcohol
3,6-dibromopyrazine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; water-d2; sodium carbonate; deuterium at 20℃; under 6000.6 Torr; for 1h; Sealed tube; | 60% |
Conditions | Yield |
---|---|
[Cp*RuCl(η2-SMe)2RuCp*(OH2)]OSO2CF3 at 60℃; for 2h; | 56% |
ethyl [2]alcohol
tris(2-diphenylphosphinoethyl)phosphine
{(P(CH2CH2P(C6H5)2)3)Fe(H)2}
Conditions | Yield |
---|---|
In tetrahydrofuran (N2) or (Ar) excess of NaBD4; addn. of C2H5OD, NMR; | A 20% B 25% C 55% |
Conditions | Yield |
---|---|
In ethyl [2]alcohol 48 h at r.t.; filtered, washed (EtOH/H2O 1:1 then H2O), dried (80°C, 72 h, 0.01 Torr); | 53% |
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