Реакция #530916

Уравнение реакции

tetrahydrofuran-ethanol

α-(1-amino-1-methylethyl)benzenemethanol

3,4-dimethoxyphenylacetic acid

EEDQ

→

2-(3,4-dimethoxyphenyl)-N-(β-hydroxy-α,α-dimethylphenethyl)acetamide

Выход 82.0%

Условия реакции

Обработка

1. 1
   ДругоеThe solution is evaporated in vacuo
2. 2
   Промывкаof ethyl acetate, washed with dilute HCl
3. 3
   Промывкаby washing with aqueous NaHCO3
4. 4
   ПромывкаSubsequently, the extract is washed with aqueous NaCl
5. 5
   Сушкаdried (Na2SO4)
6. 6
   Другоеevaporated to dryness in vacuo
7. 7
   ДругоеCrystallization of the residue from ether
8. 8
   Другоеgives 14.0 g

Методика

A solution of 8.3 g. (0.05 mole) of α-(1-amino-1-methylethyl)benzenemethanol, 9.8 g. (0.05 mole) of 3,4-dimethoxyphenylacetic acid and 13.6 g. (0.055 mole) of EEDQ (Aldrich Chem. Co.) in 300 ml. of tetrahydrofuran-ethanol is refluxed for 45 minutes and then allowed to stand for 20 hours at 25° C. The solution is evaporated in vacuo. The residue is taken up with 250 ml. of ethyl acetate, washed with dilute HCl, followed by washing with aqueous NaHCO3. Subsequently, the extract is washed with aqueous NaCl, dried (Na2SO4) and evaporated to dryness in vacuo. Crystallization of the residue from ether gives 14.0 g. (82% yield) of pure 2-(3,4-dimethoxyphenyl)-N-(β-hydroxy-α,α-dimethylphenethyl)acetamide, m.p. 123°-124° C.

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