Triethylamine → HCID 86614066, compound

Participants

Reaction Steps

To a stirred, cooled (0° C.) solution of the product of (3aS,4R,6aS,7R,10S,10aS)-7-acetyl-2,2,5,10-tetramethyl-4,6a,7,8,9,10-hexahydro-3aH-naphtho[1,8a-d][1,3]dioxol-4-yl acetate (Preparation 148, 1.8 g) in diethyl ether (30 ml) was added triethylamine (1.8 ml) and trimethylsilyltrifluoromethanesulfonate (2.3 ml). After 30 minutes, N-bromosuccinimide (1.2 g) was added and the reaction mixture was allowed to warm to room temperature over three hours. The reaction mixture was partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic phase was dried (MgSO4), evaporated and purified by flash column chromatography on silica gel using a gradient elution ethyl acetate:hexane (1:9 to 2:8) to give the product as a gum (1.81 g).

Provenance & Evidence