Ethyl Thioglycolate → (4-Formyl-phenylsulfanyl)-acetic acid ethyl ester

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Reaction Steps

The compound was prepared according to general procedure E. To a solution of ethyl-2-mercaptoacetate (1.7 mmol) in dry DMF (5 ml), sodium hydride (2.0 mmol) was added at 0° C. After 10 minutes, 4-bromobenzaldehyde (1.4 mmol) was added and the mixture was heated for 3 hours. After cooling, the solvent was removed under reduced pressure. The residue was chromatogaphed on a silica gel column (cyclohexane/ethyl acetate 9/1 as eluent) to give 188 mg of ethyl 2-(4-formylphenythio)acetate (yield 59%). 1H NMR (250 MHz, CDCl3): δ 1.23 (t, J=7.5 Hz, 3H), 3.73 (s, 2H), 4.18 (q, 2H), 7.42 (d, J=8.75 Hz, 2H), 7.76 (d, J=8.75 Hz, 2H), 9.93 (s, 1H).

Provenance & Evidence