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

HRID 1901219Notes

Reaction equation

HRID 1901219 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 Preparation 46) in a mixture of 300 ml of methanol and 700 ml of benzene, and the resulting mixture was stirred for 1 hour. At the end of this time, the solvent was removed by distillation under reduced pressure, to give the title compound having [α]D23 -119.3° (c=1.00, chloroform) and an Rf=0.36 (thin layer chromatography over silica gel, using a 1:5 by volume mixture of ethyl acetate and hexane) as a crude product.

Workup

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

Sources & evidence

ORD record
ord-2187460fed7745aa9b467bc9141f27dd
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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