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

HRID 1521799ノート

反応式

HRID 1521799 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-220c41444cac477eb4ec9c7ba1697021
出典データセット
uspto-grants-2015_07
特許番号
US09073942B2

反応ノート

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