Hydrochloric Acid → 1,1'-(4,5-Dihydronaphtho[1,2-b]thiene-2,7-diyl)di(ethan-1-one)

HRID 1521799노트

반응식

HRID 1521799 반응식
[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH2:9][CH2:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[CH:13][CH:12]=3.[Al+3].[Cl-].[Cl-].[Cl-].[C:21](Cl)(=[O:23])[CH3:22].Cl>C(Cl)Cl>[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH2:9][CH2:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[C:13]([C:21](=[O:23])[CH3:22])[CH:12]=3

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 123269761-(4,5-Dihydronaphtho[1,2-b]thiophen-2-yl)ethan-1-one

생성물 1

HCID 123269771,1'-(4,5-Dihydronaphtho[1,2-b]thiene-2,7-diyl)di(ethan-1-one)수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(4,5-dihydronaphtho[1,2-b]thiophen-2-yl)ethanone (5b) (30 g, 131 mmol) in 500 mL of DCM at 0° C., AlCl3 (52.6 g, 394 mmol) was added portion wise and after 15 min, acetyl chloride (18.69 ml, 263 mmol) was added dropwise at the same temperature over 30 min and the mixture was stirred at room temperature for 48 hr. The reaction mass was slowly added to ice water and acidified with 2 N HCl solution and extracted with DCM, and the organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound as an yellow solid (5c) (28.3 g, 80%). m/z 270.0 (M+).

후처리

  1. extractionextracted with DCM
  2. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-220c41444cac477eb4ec9c7ba1697021
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073942B2

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