Diisopropylamine → 3-[(Z)-6-methoxycarbonyl-2-hexenyl]-4-oxotetrahydropyran

To a solution of lithium diisopropylamide (2.40 mmol) in tetrahydrofuran (5 ml), prepared from diisopropylamine (0.35 ml) with n-butyllithium (1.7 ml, 1.5 M solution in hexane) using an usual manner, was added 4-oxotetrahydropyran (220 mg) in tetrahydrofuran (2 ml) at -78° C. and the mixture was stirred for 30 minutes at the same temperature. To the resulting solution was added methyl(Z)-7-bromo-5-heptenate (500 mg) in tetrahydrofuran (2 ml) at -78° C. After being stirred at room temperature for 5 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride and the solution was extracted with ethyl acetate. The organic layer was 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 (10 g) with a mixture of n-hexane and ethyl acetate (4:1) as an eluent to give 3-[(Z)-6-methoxycarbonyl-2-hexenyl]-4-oxo-tetrahydropyran (100 mg) as a colorless oil.

1. stirringAfter being stirred at room temperature for 5 hours
2. customthe reaction mixture was quenched with saturated aqueous ammonium chloride
3. extractionthe solution was extracted with ethyl acetate
4. washThe organic layer was washed successively with water and brine
5. dry with materialdried over magnesium sulfate
6. customThe solvent was evaporated in vacuo
7. customthe residue was chromatographed on a silica gel column (10 g) with a mixture of n-hexane and ethyl acetate (4:1) as an eluent

ORD record

ord-5d2b787ba24c4fef8d203bb7846913eb

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04929639