Chloroacetyl chloride → 2-chloro-N-(3,3,3-trifluoro-2-hydroxy-1-isopropyl-propyl)acetamide

To a solution of 3-amino-1,1,1-trifluoro-4-methyl-2-pentanol hydrochloride (20 g) in distilled tetrahydrofuran (480 mL) under nitrogen was added 4-methylmorpholine (21.8 mL) resulting in a white precipitate. A solution of chloroacetyl chloride (7.7 mL) in distilled tetrahydrofuran (40 mL) was added dropwise over 1 hour, and the mixture was stirred overnight. The mixture was diluted with ethyl acetate and filtered to remove undissolved solids. The filtrate was washed with 10% hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine. The solid that had been filtered was dissolved in water, the aqueous phase was extracted with ethyl acetate (twice), and the extracts were washed as the first extract had been. The organic phases were combined, dried, and evaporated to give 2-chloro-N-(3,3,3-trifluoro-2-hydroxy-1-isopropyl-propyl)acetamide as an oil (23.8 g); TLC: Rf =0.70, dichloromethane:methanol (95:5); MS: m/z=248(M+1 for 35Cl).

1. customresulting in a white precipitate
2. filtrationfiltered
3. customto remove undissolved solids
4. washThe filtrate was washed with 10% hydrochloric acid, water, saturated aqueous sodium bicarbonate and brine
5. filtrationThe solid that had been filtered
6. dissolutionwas dissolved in water
7. extractionthe aqueous phase was extracted with ethyl acetate (twice), and the extracts
8. washwere washed as the
9. extractionfirst extract
10. customdried
11. customevaporated

ORD record

ord-ecfafc213fed43ca84988d6880e93fb0

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05521179