Trimethylsilyldiazomethane → (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

HRID 1648457Notes

Reaction equation

HRID 1648457 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Cl:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C@@H:12]([OH:16])[C:13]([OH:15])=[O:14]>CCCCCC.CO.C1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C@@H:12]([OH:16])[C:13]([O:15][CH3:1])=[O:14]

Participants

6

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

Product 1

HCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

18.3 g of a 10% w/v solution of trimethylsilyldiazomethane in hexane were added dropwise to a solution of 28 g of (R)-3-chloromandelic acid [prepared as described in Step (b), above] in a mixture of 300 ml of methanol and 700 ml of benzene, and the resulting mixture was stirred for one hour. At the end of this time, the solvent was removed by distillation under reduced pressure, to give 28.6 g of the title compound having [α]D23 -119.3° (c=1.00, chloroform) and an Rf=0.36 (thin layer chromatography on silica gel, using a 1:5 by volume mixture of ethyl acetate and hexane) as a crude product. 12(d) Methyl (R)-α-t-butyldimethylsilyloxy-3-chlorophenylacetate

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-692084ceded04f928052a9db05d98cfe
Source dataset
uspto-grants-1995_07
Patent number
US05436257

Reaction notes

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