Sodium Chloride → 6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-ol

Participants

Reaction Conditions

Reaction Steps

275 ml of a toluene solution of 1.2M of diisobutyl aluminium hydride were slowly added at -60° C. to a mixture of 62.16 g of 6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-one [prepared by method of Ver Nooy et al, J.A.C.S., Vol. 77 (1955), p. 3583] and 500 ml of toluene and the mixture was stirred at -60° C. for 45 minutes and was then poured into aqueous 1M sodium potassium double tartrate. The mixture was stirred for 2 hours and the decanted aqueous phase was saturated with sodium chloride and extracted with methylene chloride. The combined organic phases were evaporated to dryness under reduced pressure to obtain 64.7 g of racemic 6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-ol melting at 104° C.

Provenance & Evidence