Potassium Bromide → HCID 23245525, compound

Participants

Reaction Steps

To a solution of 27.50 g of (1R,3S,5R)-2,2-dimethyl-propionic acid 3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclohexyl ester in 250 ml of dichloromethane was subsequently added at 0° a solution of 0.713 g of KBr and 2.656 g of NaHCO3 in 250 ml of water and 200 mg of 2,2,6,6-tetramethyl-piperidine-1-oxyl, radical. The stirred mixture was treated at 0° with 61.9 g of NaOCl (11.0%) over 1 h after which time t.l.c. showed completion of the reaction. The layers were separated, the organic layer was washed with 15% aqueous NaCl, dried over MgSO4 and evaporated to give 27.24 g of the pure (t.l.c.) title compound as a yellow oil. IR (neat): 1728s (C═O). MS (EI): 271/5 (M-tert-butyl).

Provenance & Evidence