Hexane → HCID 68299233, compound

Temperature

-60 °C

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.

1. temperatureto warm to 10° C. over 2 h
2. customThe reaction was quenched with saturated ammonium chloride
3. customthe solvent was removed under reduced pressure
4. customThe residue was partitioned between water and chloroform
5. dry with materialthe organic layer dried with sodium sulfate
6. customevaporated
7. customThe residue was purified by column chromatography on silica gel

ORD record

ord-296c6fc30aac4cbd85b02130d5e6b4ed

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946453B2