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

Participants

Reaction Steps

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

Provenance & Evidence