Tetrahydrofuran → HCID 19736369, compound

Participants

Reaction Steps

A mixture of 4-(2,5,6,6-tetramethyl-1-cyclohexen-1-yl)-2-butanone (13 g, 0.061 mol) and propargylic alcohol (4 g, 0.071 mol) was added within 100 min to a mechanically stirred slurry of powdered KOH (26 g, 0.46 mol) in THF (100 ml) at 20° C. under N2. After 3 h at 20°, the brown mixture was poured into a cold solution of NH4Cl (28 g) in H2O (100 ml). Extraction with ether, workup and chromatography [SiO2, (200 g), cyclohexane/ethyl acetate 7:3] afforded 4-methyl-6-(2,5,6,6-tetramethyl-1-cyclohexen-1-yl)-2-hexyn-1,4-diol as a viscous pale-yellow oil (12.3 g, 77%).

Provenance & Evidence