Hydrochloric Acid → HCID 68826874, compound

Participants

Reaction Steps

A solution of 3-methyl-1,5-cyclohexadecanedione (33) (1 g, 3.76 mmol) in CH2Cl2 (6 ml) was treated at 22-24° with a solution of ZrCl3OPr (36% in AcOBu) (3 g, 5.0 mmol). After 15 minutes the solution was treated at −10° C. with NBu3 (1.15 g, 1.48 ml, 6.2 mmol). After 60 minutes, the reaction mixture was poured into 15 ml water and 15 ml of a 2 N HCl solution were added. After extraction with 50 ml diethyl ether the combined organic phases were washed (saturated aqueous NaHCO3 solution, H2O), dried (Na2SO4) and the solvent was evaporated (crude 1.0 g). Flash chromatography, using SiO2 (100 g) and n-pentane/diethyl ether=6:4 as eluent, afforded 898 mg (yield: 90%) of (34).

Provenance & Evidence