Ethyl Acetate → HCID 45091277, compound

Temperature

-70 °C

A solution of 6-methoxy-chroman-2-one (3.66 g, 20.53 mmol) in 300 ml of dichloromethane was cooled to −70° C., and a solution of diisobutylaluminium hydride (40 ml of a 1M solution in toluene, 40 mmol) was added dropwise. The solution was stirred at −70° C. for 2 h, and then ethyl acetate (10 ml) was added. After stirring for 15 min, 200 ml of a saturated solution of Rochelle salt was added dropwise, and the mixture was warmed to room temperature. 200 ml of ethyl acetate were added, and the mixture was stirred vigorously for 2 h and then decanted. The organic layer was washed with water and brine and dried with sodium sulfate, and the solvent removed under reduced pressure. The crude product was purified by chromatography on silica gel (ethyl acetate in cyclohexane) to afford 2.90 g of white crystals (78%).

1. stirringAfter stirring for 15 min
2. temperaturethe mixture was warmed to room temperature
3. stirringthe mixture was stirred vigorously for 2 h
4. customdecanted
5. washThe organic layer was washed with water and brine
6. dry with materialdried with sodium sulfate
7. customthe solvent removed under reduced pressure
8. customThe crude product was purified by chromatography on silica gel (ethyl acetate in cyclohexane)

ORD record

ord-4f007dd236b846798807af435029a2c0

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08912224B2