Water → HCID 22990118, compound

To 7-(4-methylphenyl)-2,3,4,5-tetrahydro-1-benzooxepin-5-one (1 g) dissolved in ethanol (50 ml) was added under ice cooling sodium borohydride (0.3 g). The resulting mixture was stirred at room temperature for 30 minutes, was mixed with water and was concentrated. The residue was extracted with ethyl acetate, and the organic layer was washed with water and was then concentrated. To the residue dissolved in bis(2-methoxyethyl)ether (20 ml) was added hydrochloric acid (5 ml), and the resulting mixture was stirred with heating at 75° C. for one hour. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, was then dried with anhydrous magnesium sulfate and was evaporated to remove the solvent. The precipitate was collected by filtration using hexane to obtain 7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine (0.78 g) as colorless crystals.

1. additionwas added under ice
2. concentrationwas concentrated
3. extractionThe residue was extracted with ethyl acetate
4. washthe organic layer was washed with water
5. concentrationwas then concentrated
6. dissolutionTo the residue dissolved in bis(2-methoxyethyl)ether (20 ml)
7. additionwas added hydrochloric acid (5 ml)
8. stirringthe resulting mixture was stirred
9. temperaturewith heating at 75° C. for one hour
10. additionThe reaction mixture was poured into water
11. extractionwas extracted with ethyl acetate
12. washThe organic layer was washed with water
13. dry with materialan aqueous saturated solution of sodium chloride, was then dried with anhydrous magnesium sulfate
14. customwas evaporated
15. customto remove the solvent
16. filtrationThe precipitate was collected by filtration

ORD record

ord-f83972715eef4474a805fcd955b3e0b6

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627651B1