Sodium Hydroxide → HCID 66615728, compound

Participants

Reaction Conditions

Reaction Steps

At −70° C., a suspension of lithium aluminium hydride (0.52 g, 13.7 mmol) in diethyl ether (30 ml) was treated dropwise within 10 min. with a solution of (−)-rotundone ((3S,5R,8S)-3,4,5,6,7,8-hexahydro-3,8-dimethyl-5-(1-methylethenyl)-1(2H)-azulenone; 3.0 g, 13.7 mmol) in diethyl ether (20 ml). The resulting mixture was stirred for 1 h at −70° C., treated dropwise with a 2M aqueous NaOH solution (2.5 ml) while the reaction temperature rose to −20° C., stirred for 20 min., treated with MgSO4 (5 g), stirred for 10 min., filtered, and the solvent evaporated. Flash chromatography (400 g 0.015-0.040 mm-SiO2, flow: 80 ml/min., hexane/methyl t-butyl ether 100:0 to 85:15 in 30 min.) of the crude product (2.8 g, GC: 65:35 (1R)/(1S)-epimer) gave (1R,3S,5R,8S)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulen-1-ol (1.07 g, 35%) and (1S,3S,5R,8S)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulen-1-ol (0.64 g, 21%).

Provenance & Evidence