Sodium hydride → 3-[(Z)-6-methoxycarbonyl-2-hexenyl]-4-methoxymethylenetetrahydropyran

To a solution of (methoxymethyl)triphenylphosphonium chloride (3.17 g) in dimethylsulfoxide (20 ml) was added dimsyl sodium prepared from sodium hydride (370 mg, 60% in oil) with dimethylsulfoxide (25 ml) at room temperature. After being stirred at room temperature for 30 minutes, to the resulting mixture was added 3-[(Z)-6-methoxycarbonyl-2-hexenyl]-4-oxotetrahydropyran (740 mg) in dimethylsulfoxide (2 ml) and the solution was stirred at room temperature for additional 4 hours. The reaction mixture was poured into a mixture of water (100 ml) and ethyl acetate (100 ml) and the organic layer was separated, washed successively with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column (30 g) with a mixture of n-hexane and ethyl acetate (4:1) as an eluent to give 3-[(Z)-6-methoxycarbonyl-2-hexenyl]-4-methoxymethylenetetrahydropyran (279 mg) as a colorless oil.

1. stirringthe solution was stirred at room temperature for additional 4 hours
2. customthe organic layer was separated
3. washwashed successively with water and brine
4. dry with materialdried over magnesium sulfate
5. customThe solvent was evaporated in vacuo
6. customthe residue was chromatographed on a silica gel column (30 g) with a mixture of n-hexane and ethyl acetate (4:1) as an eluent

ORD record

ord-9f5bcb74d4c14d2eba013b93f32e53df

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04929639