Hydrochloric Acid → HCID 19045400, compound

Methylmagnesium chloride (2.8M in THF, 21 ml, 60 mmol) was added dropwise to an ice-cooled solution of 2-oxepanone (2.22 ml, 2.28 g, 20 mmol) in THF (20 ml). The mixture was stirred for 1 hour, then water (100 ml) was added dropwise. The pH was adjusted to 7 with aqueous HCl (3N) and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. Dichloromethane (20 ml) and pyridine (3.24 ml, 3.16 g, 40 mmol) were added and the mixture was cooled in ice. Methanesulfonyl chloride (1.55 ml, 2.29 g, 20 mmol) was added dropwise and the mixture was stirred at room temperature for 3 hours. Dichloromethane (50 ml) was added and the mixture was washed with aqueous HCl (2M, 50 ml) and aqueous sodium hydrogen carbonate (saturated, 50 ml), dried (Na2SO4) and evaporated under reduced pressure to give the alcohol as a pale yellow oil (4.38 g, 98%).

1. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
2. dry with materialThe combined organic fractions were dried (Na2SO4)
3. customevaporated under reduced pressure
4. temperaturethe mixture was cooled in ice
5. stirringthe mixture was stirred at room temperature for 3 hours
6. washthe mixture was washed with aqueous HCl (2M, 50 ml) and aqueous sodium hydrogen carbonate (saturated, 50 ml)
7. dry with materialdried (Na2SO4)
8. customevaporated under reduced pressure

ORD record

ord-dc5425ac52664f45bee53207c04e56a8

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05633247