تفاعل #77663

معادلة التفاعل

N-(1,1-dimethyl-2-phenyl-ethyl)-2,2,2-trifluoroacetamide

Tetrabutylammonium tribromide

methanol

→

pure product

المردود 41.0%

N-[2-(Bromoacetyl-phenyl)-1,1-dimethyl-ethyl]-2,2,2-trifluoroacetamide

المردود 41.0%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىThe volatiles were then removed in vacuo to an oil, which
2. 2
   استخلاصextracted with 125 ml of saturated aqueous sodium bicarbonate
3. 3
   غسيلthe combined organic extracts were then washed with water
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe crude oil was purified by column chromatography (silica gel; 60% methylene chloride/hexanes to 10% ethyl acetate/methylene chloride)
8. 8
   أخرىthe resulting material (5.18 g) was recrystallized from hexanes

الإجراء التجريبي

In a round-bottomed flask, N-(1,1-dimethyl-2-phenyl-ethyl)-2,2,2-trifluoroacetamide (6.90 g, 21.0 mmol) was dissolved in methylene chloride (66 ml) and methanol (33 ml). Tetrabutylammonium tribromide (10.6 g, 22.0 mmol) was added to this solution in one portion, and the mixture was allowed to stir at room temperature overnight. The volatiles were then removed in vacuo to an oil, which was then resuspended in 100 ml of methylene chloride and extracted with 125 ml of saturated aqueous sodium bicarbonate. The aqueous extracts were reextracted with methylene chloride (3×10 ml), and the combined organic extracts were then washed with water and dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude oil was purified by column chromatography (silica gel; 60% methylene chloride/hexanes to 10% ethyl acetate/methylene chloride), and the resulting material (5.18 g) was recrystallized from hexanes to afford 3.14 g (41% yield) of pure product as a fluffy white solid.

المصدر