反応 #530916

反応方程式

tetrahydrofuran-ethanol

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

3,4-dimethoxyphenylacetic acid

EEDQ

→

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

収率 82.0%

反応条件

後処理

1. 1
   その他The solution is evaporated in vacuo
2. 2
   洗浄of ethyl acetate, washed with dilute HCl
3. 3
   洗浄by washing with aqueous NaHCO3
4. 4
   洗浄Subsequently, the extract is washed with aqueous NaCl
5. 5
   乾燥dried (Na2SO4)
6. 6
   その他evaporated to dryness in vacuo
7. 7
   その他Crystallization of the residue from ether
8. 8
   その他gives 14.0 g

実験手順

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.

出典