Benzyl mercaptan → HCID 19605253, compound

Participants

Reaction Conditions

Reaction Steps

Sodium (8.1 g, 0.35 mol) was dissolved in ethanol (250 ml) and benzyl mercaptan (45.2 g, 0.37 mol) added dropwise over 20 minutes keeping the temperature between 20° C.-25° C. whilst bubbling nitrogen through the mixture. After 15 minutes, the reaction was cooled to 5° C. and a solution of 4-acetoxyazetidin-2-one (45.0 g, 0.35 mol) in ethanol (50 ml) was added dropwise over 15 minutes whist maintaining the temperature at 5° C. The mixture was stirred at room temperature for 60 minutes and evaporated to dryness under reduced pressure. Water (500 ml) was added, the mixture extracted with dichloromethane (2×300 ml), the extracts dried (MgSO4) and evaporated under reduced pressure to an oil. The oil was cooled to -20° C. and titurated with ether (400 ml) to give a white solid which was isolated by filtration (50.2 g, 79%), mp 50-51.0° C.

Provenance & Evidence