反応 #530917

反応方程式

3,4-dimethoxyphenylacetic acid

EEDQ

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

→

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

収率 72.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他Tetrahydrofuran is evaporated in vacuo
2. 2
   抽出The amide is extracted twice with 500 ml
3. 3
   洗浄The combined organic extracts are washed with 500 ml
4. 4
   乾燥dilute aqueous NH4OH solution, dried (Na2SO4)
5. 5
   その他evaporated to dryness in vacuo
6. 6
   workup.DISSOLUTIONThe residual oil is dissolved in hot diethyl ether from which it
7. 7
   その他crystallizes
8. 8
   その他to give 72.0 g
9. 9
   その他Recrystallization from diethyl ether
10. 10
    その他gives 70 g

実験手順

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.

出典