Acetic Acid → 2-Methylpentane

Participants

Reaction Conditions

Reaction Steps

(3-Formyl-phenyl)-acetic acid methyl ester (0.64 g), acetic acid (0.18 mL) and 4-phenyl-piperidine (0.48 mL) were combined in dichloromethane (10 mL). After 1 hour, sodium triacetoxyborohydride (0.95 g) was added and the reaction stirred overnight. After 24 hours, the solvent was evaporated. The resultant residue was loaded onto a conditioned SCX cartridge (10 g, Varian) and washed with methanol (50 mL), then eluted with methanolic ammonia solution (2M, 50 mL). The elution fraction was evaporated and the residue was dissolved in ethanol (10 mL). Calcium chloride anhydrous (0.67 g) was added followed by sodium borohydride (0.45 g) and the resulting mixture stirred overnight. An aqueous potassium carbonate solution (2M, 50 mL) was added and the ethanol evaporated. The aqueous was extracted with ethyl acetate (3×50 mL) and the combined organics washed with water (50 mL), brine (50 mL), dried (sodium sulfate) and evaporated. The residue was redissolved in tetrahydrofuran (10 mL) and cooled to 0° C., under nitrogen. Borane-methyl sulfide complex (2M solution in tetrahydrofuran, 2.25 mL) was added and the resulting mixture stirred for 5 min. The tetrahydrofuran was evaporated and the residue purified on silica, eluting with diethyl ether: iso-hexane [1:1 to 1:0] to give subtitle product, as an oil 193 mg.

Provenance & Evidence