تفاعل #1149574

معادلة التفاعل

2-chlorodimethylacetamide

Tetrabutylammonium fluoride

(R)-N-(2-chloro-4-(triisopropylsilylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Ethyl acetate

→

title compound

(R)-N-[2-Chloro-4-(N,N-dimethylcarbamoylmethylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm up
2. 2
   غسيلthe mixture was washed with brine (100 ml)
3. 3
   أخرىthen dried
4. 4
   أخرىvolatile material was removed by evaporation
5. 5
   أخرىThe residue was purified on a silica gel Mega Bond Elut column
6. 6
   غسيلeluting with 10-50% ethyl acetate/hexane

الإجراء التجريبي

Tetrabutylammonium fluoride (1.1 ml of a 1M solution in THF) was added to (R)-N-(2-chloro-4-(triisopropylsilylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 28) (0.50 g) in anhydrous THF (5 ml) at −70° C. After 15 minutes 2-chlorodimethylacetamide (0.17 ml) was added and the mixture was allowed to warm up then was stirred at ambient temperature for 45 minutes. Ethyl acetate (80 ml) was added and the mixture was washed with brine (100 ml) then dried and volatile material was removed by evaporation. The residue was purified on a silica gel Mega Bond Elut column eluting with 10-50% ethyl acetate/hexane to give the title compound (0.30 g) as a solid. NMR (CDCl3) 1.72 (s, 3H), 2.97 (s, 3H), 3.08 (s, 3H), 3.71 (s, 2H), 4.76 (s, 1H), 7.32-7.36 (m, 1H), 7.53 (d, 1H), 8.32 (d, 1H), 9.05 (s, 1H); MS (ESP−): 383.

المصدر