反応 #76847

反応方程式

triethylamine

bromo-phenyl-acetic acid methyl ester

AcOEt hexane

1-(4,5-dimethoxybenzyl)6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-hydrochloride

→

title product

収率 91.4%

1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid methyl ester

収率 91.4%

溶媒

CH2Cl2

toluene

反応条件

後処理

1. 1
   温度at reflux under argon for 20 h
2. 2
   温度After cooling
3. 3
   洗浄washed with water
4. 4
   抽出The aqueous phase was extracted twice with CH2Cl2
5. 5
   乾燥the combined organic phases were dried over anhydrous MgSO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他to give a crude brown-orange oil

実験手順

To a white suspension of 1-(4,5-dimethoxybenzyl)6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-hydrochloride (5 g, 0.013 mol) in dry toluene (50 ml), were added triethylamine (5.5 ml, 0.039 mol) and bromo-phenyl-acetic acid methyl ester (2.07 ml, 0.013 mol). The reaction mixture was stirred at reflux under argon for 20 h. After cooling, the mixture was diluted in CH2Cl2 and washed with water. The aqueous phase was extracted twice with CH2Cl2, the combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude brown-orange oil. Flash chromatography (AcOEt/hexane 1/1) gave 5.85 g (90%) of the title product as a brown-orange oil.

出典