Hydrogen Peroxide → HCID 59289018, compound

Participants

Reaction Conditions

Reaction Steps

4′-pent-4-enyl-4-propyl-bicyclohexyl [JP10046150] (9.9 g, 36 mmol) in THF (200 ml) are cooled to 0° C. and a 0.5 M solution of 9-BBN in THF (100 ml, 50 mmol) is added dropwise. The reaction is stirred overnight at room temp., cooled to −20° C. and 30% hydrogen peroxide (12 ml, 0.11 mol) are added followed by 32% aq. sodium hydroxide (7 ml, 76 mmol). The cooling bath is removed and the reaction is stirred overnight. Water is added and the mixture is extracted three times with ethyl acetate. The combined org. layers are washed with water and brine and are dried (Na2SO4). The solvent is evaporated and the crude product is recrystalised from ethanol to give 5-(4′-propyl-bicyclohexyl-4-yl)-pentan-1-ol as colourless crystals.

Provenance & Evidence