Hexane → HCID 68299233, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (methoxymethyl)triphenylphosphonium chloride (35.8 g, 104 mmol) in THF (160 mL) was cooled to −60° C. and treated with a 2.5M solution of n-BuLi in hexane (42 mL, 105 mmol). After 20 min, a solution of 1-methoxy-piperidin-4-one [prepared according to Journal of Organic Chemistry (1961), 26, 1867-74] (9 g, 70 mmol) in THF (80 mL) was added, and the reaction mixture was allowed to warm to 10° C. over 2 h. The reaction was quenched with saturated ammonium chloride, and the solvent was removed under reduced pressure. The residue was partitioned between water and chloroform and the organic layer dried with sodium sulfate and evaporated. The residue was purified by column chromatography on silica gel. Yield: 9.2 g of 1-methoxy-4-methoxymethylene-piperidine as an oil.

Provenance & Evidence