반응 #530916

반응 방정식

tetrahydrofuran-ethanol

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

3,4-dimethoxyphenylacetic acid

EEDQ

→

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

수율 82.0%

반응 조건

후처리

1. 1
   기타The solution is evaporated in vacuo
2. 2
   세척of ethyl acetate, washed with dilute HCl
3. 3
   세척by washing with aqueous NaHCO3
4. 4
   세척Subsequently, the extract is washed with aqueous NaCl
5. 5
   건조dried (Na2SO4)
6. 6
   기타evaporated to dryness in vacuo
7. 7
   기타Crystallization of the residue from ether
8. 8
   기타gives 14.0 g

실험 절차

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.

출처