Reaktion #530916

Reaktionsgleichung

tetrahydrofuran-ethanol

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

3,4-dimethoxyphenylacetic acid

EEDQ

→

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

Ausbeute 82.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution is evaporated in vacuo
2. 2
   Waschenof ethyl acetate, washed with dilute HCl
3. 3
   Waschenby washing with aqueous NaHCO3
4. 4
   WaschenSubsequently, the extract is washed with aqueous NaCl
5. 5
   Trocknendried (Na2SO4)
6. 6
   Sonstigeevaporated to dryness in vacuo
7. 7
   SonstigeCrystallization of the residue from ether
8. 8
   Sonstigegives 14.0 g

Vorschrift

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.

Quelle