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

HRID 48569

反応式

HRID 48569 の反応式
Cl.[CH3:2][O:3][C:4]1[C:24]([O:25][CH3:26])=[CH:23][C:7]([CH2:8][CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH2:12][CH2:11]N2)=[CH:6][CH:5]=1.[CH2:27](N(CC)CC)C.[CH3:34][O:35][C:36](=[O:45])[CH:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:34][O:35][C:36](=[O:45])[CH2:37][C:38]1([CH:27]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[CH:9]2[CH2:8][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[C:24]([O:25][CH3:26])[CH:23]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH2:39]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 16667431Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-, hydrochloride (1:1)HCID 21226206Ethyl acetate hexane

生成物 1

HCID 697601251-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid methyl ester収率 91.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

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.

後処理

  1. temperatureat reflux under argon for 20 h
  2. temperatureAfter cooling
  3. washwashed with water
  4. extractionThe aqueous phase was extracted twice with CH2Cl2
  5. dry with materialthe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude brown-orange oil

出典と根拠

ORDレコード
ord-ea68a220f4284ba196011734ad7e3a3e
出典データセット
uspto-grants-2004_03
特許番号
US06703392B2

関連ノート

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