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

HRID 1513893

반응식

HRID 1513893 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-5 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c186b5165a2843f0a1f2cb85c2ed2f99
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217032B2

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