반응 #530917

반응 방정식

3,4-dimethoxyphenylacetic acid

EEDQ

α-(1-amino-1-methylethyl)-3-methoxybenzenemethanol

→

N-(β-hydroxy-3-methoxy-α,α-dimethylphenethyl)-3,4-dimethoxybenzeneacetamide

수율 72.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타Tetrahydrofuran is evaporated in vacuo
2. 2
   추출The amide is extracted twice with 500 ml
3. 3
   세척The combined organic extracts are washed with 500 ml
4. 4
   건조dilute aqueous NH4OH solution, dried (Na2SO4)
5. 5
   기타evaporated to dryness in vacuo
6. 6
   workup.DISSOLUTIONThe residual oil is dissolved in hot diethyl ether from which it
7. 7
   기타crystallizes
8. 8
   기타to give 72.0 g
9. 9
   기타Recrystallization from diethyl ether
10. 10
    기타gives 70 g

실험 절차

A solution of 50 g. (0.26 mole) of 3,4-dimethoxyphenylacetic acid, 68 g. (0.28 mole) of EEDQ and 50 g. (0.26 mole) of α-(1-amino-1-methylethyl)-3-methoxybenzenemethanol in 450 ml. tetrahydrofuran are stirred for three days at 25° C., and then heated for 5 hours at 65° C. Tetrahydrofuran is evaporated in vacuo, and the residue is taken up with ice and 10% aqueous H2SO4 solution to pH 2. The amide is extracted twice with 500 ml. ethyl acetate. The combined organic extracts are washed with 500 ml. dilute aqueous NH4OH solution, dried (Na2SO4) and evaporated to dryness in vacuo. The residual oil is dissolved in hot diethyl ether from which it crystallizes to give 72.0 g. of impure product. Recrystallization from diethyl ether gives 70 g. (72% yield) of N-(β-hydroxy-3-methoxy-α,α-dimethylphenethyl)-3,4-dimethoxybenzeneacetamide as white crystals of analytical purity, m.p. 137°-138° C.

출처