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 (Na2SO 4) 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 (Na2SO 4)
8. customevaporated under reduced pressure

ORD record

ord-d978b9f3cc1040ca8a6a68a52eb739a9

Source dataset

uspto-grants-1993_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05206240