Ethyl 4-thiomethylbenzoylformate → Hydroxy-(4-methylsulfanyl-phenyl)-acetic acid ethyl ester

Participants

Reaction Steps

To a solution of (4-methylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (Described in J. Med. Chem. 1981, 407) (1.0 eq) in EtOH (0.22M) at −78° C. was added NaBH4 (0.5 eq). The resulting mixture was stirred for 30 min then quenched at −78° C. by adding saturated aqueous NH4Cl. The residual mixture was concentrated, filtered on silica gel using EtOAc. The combined organic extracts were concentrated and the residual solid was recrystallised in Et2O/Hex to afford the desired compound as a yellow solid.

Provenance & Evidence