Acetone → HCID 86737362, compound

Participants

Reaction Steps

An excess of Jones reagent (4 ml, 4 mM) is added slowly to a mixture of (1RS,4SR,5RS)-4-methyl-4-[4-methyl-5-(tetrahydropyran-2-yloxy)pentyl]-3,8-dioxabicyclo [3.2.1] octane-1-acetaldehyde (813 mg, 2.3 mM) and acetone (20 ml) at 0° C. The resulting mixture is stirred for thirty minutes and treated with 2-propanol (2 ml) followed by ethyl acetate (50 ml) and water (20 ml). The organic layer is separated and the aqueous layer is extracted with ethyl acetate (3×20 ml). The combined organic layers are dried (sodium sulfate) and the solvent is removed in vacuo to give a pale yellow oil. The oil is redissolved in ether (15 ml), treated with an excess of diazomethane in ether and stirred for ten minutes. The solvent is removed in vacuo to give methyl (1RS,4SR,5RS)-4-methyl-4-[4-methyl-5-(tetrahydropyran-2-yloxy)pentyl]-3,8-dioxabicyclo [3.2.1] octane-1-acetate as a pale yellow oil (625 mg, 83%). This material is homogeneous by thin layer chromatography and is used directly in the next step.

Provenance & Evidence