Gamma-Butyrolactone → 4-Hydroxy-1-(3-pyridyl)-1-butanone

A solution of 10.0 g (63.3 mmol) of 3-bromopyridine in 100 ml of ether was cooled to -78° C., to which 40 ml (64 mmol) of 1.6M n-butyllithium hexane solution was added dropwise with stirring. After completion of the addition, the mixture was stirred for further 15 minutes, to which the solution of 5.45 g (63.3 mmol) of γ-butyrolactone in 15 ml of ether was added dropwise, and stirred for further 1 hour at -78° C.-room temperature. To the reaction mixture an aqueous solution of ammonium chloride, and the resultant substance was extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was evaporated off. The residue was purified with silica gel column chromatography (CHCl3 -MeOH (9:1)) and recrystallized from ethyl acetate-isopropyl ether, to give 8.0 g (77%) of 4-(3-pyridyl)-4-oxobutanol. m.p. 36°-37° C.

1. additionwas added dropwise
2. additionAfter completion of the addition
3. additionwas added dropwise
4. stirringstirred for further 1 hour at -78° C.-room temperature
5. extractionTo the reaction mixture an aqueous solution of ammonium chloride, and the resultant substance was extracted with ethyl acetate
6. washThe extract was washed with water
7. customdried
8. customthe solvent was evaporated off
9. customThe residue was purified with silica gel column chromatography (CHCl3 -MeOH (9:1))
10. customrecrystallized from ethyl acetate-isopropyl ether

ORD record

ord-be0ba787c6af4d0ea17b05627ff9ce40

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04851413