Hydrochloric Acid → HCID 11436260, compound

Participants

Reaction Steps

When the reaction was done with (18), (19) or (27), the reaction mixture, obtained above after a conversion of about 40%, can be alternatively treated 10 minutes with a mixture of 0.4 ml H2O and 0.4 ml of an aqueous 1N HCl solution. After extraction of the aqueous layer with diethyl ether the organic layer was washed (saturated aqueous NaHCO3 solution, H2O), dried over MgSO4 and filtered. The solvent was removed under vacuum and the residue was purified by flash chromatography to yield in the desired product, i.e. (1R,11S,14R)-1-hydroxy-14-methyl-bicyclo[9.4.0]pentadecan-12-one or (1S,11R,14S)-1-hydroxy-14-methyl-bicyclo[9.4.0]pentadecan-12-one or an optically active mixture of said stereoisomers depending on the configuration of the alkoxide and (S)-14-methyl-bicyclo[9.4.0]pentadec-1(11)-en-12-one or (R)-14-methyl-bicyclo[9.4.0]pentadec-1(11)-en-12-one or an optically active mixture of said stereoisomers depending on the configuration of the alkoxide.

Provenance & Evidence