Water → [4-(2-Azepan-1-yl-ethoxy)-phenyl]-(2-hydroxy-6-methoxy-naphthalen-1-yl)-methanone

HRID 1513893

反応式

HRID 1513893 の反応式
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:20][O:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([O:32]C)[CH:28]=2)[CH:23]=1.[Cl-].[Cl-].[Cl-].[Al+3].O>ClCCl>[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([C:28]3[C:29]4[C:24](=[CH:23][C:22]([O:21][CH3:20])=[CH:31][CH:30]=4)[CH:25]=[CH:26][C:27]=3[OH:32])=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 962WaterHCID 796272,6-DimethoxynaphthaleneHCID 6451240Aluminum(III) ChlorideHCID 227430554-(2-Azepan-1-yl-ethoxy)-benzoyl chloride

生成物 1

HCID 67004584[4-(2-Azepan-1-yl-ethoxy)-phenyl]-(2-hydroxy-6-methoxy-naphthalen-1-yl)-methanone収率 85.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-5 °C

実験手順

Dissolve 4-(2-azepan-1-yl-ethoxy)-benzoyl chloride (79.4 g, 249 mmol) and 2,6-dimethoxynaphthalene (37.8 g, 201 mmol) in dichloromethane (800 ml). Cool to −5° C. and add aluminum trichloride (134 g, 1 mol). Warm to room temperature and stir overnight. Add chilled water (1.5 L) and stir vigorously for 1 hour. Decant the mixture away from the residue and separate organic. Wash the aqueous layer with dichloromethane (500 mL). Combine with residue from the reaction vessel and wash with saturated aqueous sodium bicarbonate (1 L). Separate the organic after prolonged stirring (2 hours) and wash the aqueous layer with dichloromethane (300 mL). Combine the organic layers and add Darco (30 g), silica gel (30 g), and magnesium sulfate. Filter and concentrate in vacuo to give 72.4 g of [4-(2-azepan-1-yl-ethoxy)-phenyl]-(2-hydroxy-6-methoxy-naphthalen-1-yl)-methanone (73%).

後処理

  1. temperatureWarm to room temperature
  2. additionAdd
  3. stirringstir vigorously for 1 hour
  4. customDecant the mixture away from the residue
  5. customseparate organic
  6. washWash the aqueous layer with dichloromethane (500 mL)
  7. washCombine with residue from the reaction vessel and wash with saturated aqueous sodium bicarbonate (1 L)
  8. customSeparate the organic
  9. stirringafter prolonged stirring (2 hours)
  10. washwash the aqueous layer with dichloromethane (300 mL)
  11. additionCombine the organic layers and add Darco (30 g), silica gel (30 g), and magnesium sulfate
  12. filtrationFilter
  13. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-c186b5165a2843f0a1f2cb85c2ed2f99
出典データセット
uspto-grants-2012_07
特許番号
US08217032B2

関連ノート

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