Réaction #530916

Équation de réaction

tetrahydrofuran-ethanol

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

3,4-dimethoxyphenylacetic acid

EEDQ

→

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

Rendement 82.0%

Conditions de réaction

Traitement

1. 1
   AutreThe solution is evaporated in vacuo
2. 2
   Lavageof ethyl acetate, washed with dilute HCl
3. 3
   Lavageby washing with aqueous NaHCO3
4. 4
   LavageSubsequently, the extract is washed with aqueous NaCl
5. 5
   Séchagedried (Na2SO4)
6. 6
   Autreevaporated to dryness in vacuo
7. 7
   AutreCrystallization of the residue from ether
8. 8
   Autregives 14.0 g

Mode opératoire

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.

Source