Acetic Acid → 5-tert-butoxy-5-oxo-3-[(phenylthio)methyl]pentanoic Acid

Participants

Reaction Conditions

Reaction Steps

The product from step 1(200 mg, 1.0 mmoles) and thio phenol (110 mg, 1 mmoles) were combined in dimethyl formamide (1.5 mL) at room temperature. Lithium (bis trimethyl silyl) amide (1.25 mL of a 1M solution in THF) was added and the reaction heated at 80° C. for 18 h. Reaction was diluted with water, made acidic with acetic acid and extracted with dichloromethane 2×40 mL. The combined extracts were washed with water 2×50 mL, brine 1×50 mL, dried and the solvent removed under pressure. The crude was chromatographed to give the product 108 mg (35%). MS (ESI+) for C16H22O4S m/z 333 (M+Na)+.

Provenance & Evidence