Tetrahydrofuran → tert-butyl (3R)-4-hydroxy-3-methylbutyrate

Participants

Reaction Conditions

Reaction Steps

Borane-dimethyl sulphide complex (10M, 10.3 ml) was added over 15 min to a stirred mixture of 1-tert-butyl (3R)-3-methylsuccinate (12.9 g) and THF (200 ml) which had been cooled to -10° C. and placed under an atmosphere of argon. The mixture was stirred at -10° C. for 30 min. The mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture was recooled to 5 C. and methanol (50 ml) was added portionwise. The mixture was allowed to warm to room temperature and stirred for 30 min. The mixture was evaporated and the residue partitioned between dichloromethane (100 ml) and water (100 ml). The organic phase was filtered through phase separating paper and evaporated to give tert-butyl (3R)-4-hydroxy-3-methylbutyrate as an oil (11 g); NMR (CDCl3) δ 3.55(2H,m), 2.1-2.4(3H,m), 1.46(9H,s), 0.98(3H,d).

Provenance & Evidence