1-Fluoronaphthalene → Ethyl 6-(4-fluoro-1-naphthyl)-6-oxohexanoate

HRID 563107

반응식

HRID 563107 반응식
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Cl-].[CH2:13]([O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:24])=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 94501-FluoronaphthaleneHCID 6451240Aluminum(III) ChlorideHCID 86624202Adipic acid monoethyl ester chloride

생성물 1

HCID 18174724Ethyl 6-(4-fluoro-1-naphthyl)-6-oxohexanoate수율 69.8%

실험 절차

To a mixture of 1-fluoronaphthalene (20.0 g) and adipic acid monoethyl ester chloride (27.5 g) was added gradually aluminum chloride (38.5 g) with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water (500 ml) and extracted with diethyl ether (200 ml×2). The organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (200 ml), dried over anhydrous magnesium sulfate, and concentrated to give ethyl 6-(4-fluoro-1-naphthyl)-6-oxohexanoate as an oil (27.7 g, 67%).

후처리

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 2 hours
  3. extractionextracted with diethyl ether (200 ml×2)
  4. washThe organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (200 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2c34d0d514114919bc9d037427b90e54
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067453B2

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