Water → (4'-Bromobiphenyl-4-yl)acetone

HRID 1626789ノート

反応式

HRID 1626789 の反応式
C[Li].C([O:5][CH2:6][CH3:7])C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21]C(N(OC)C)=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.O>O1CCCC1>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:6](=[O:5])[CH3:7])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 866700832-(4'-Bromobiphenyl-4-yl)-N-methoxy-N-methylacetamideHCID 178418348HCID 178418348、化合物

生成物 1

HCID 68193283(4'-Bromobiphenyl-4-yl)acetone収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of methyllithium in diethyl ether (40 mL, 44 mmol) was diluted with tetrahydrofuran (120 mL), and a solution of 2-(4′-bromobiphenyl-4-yl)-N-methoxy-N-methylacetamide (12 g, 37 mmol) in tetrahydrofuran (50 mL) was added at −78° C., followed by stirring at the same temperature for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (7.6 g, 26 mmol) as a white solid (yield 71%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. distillationsubsequently the solvent was distilled off under reduced pressure
  3. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.50 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-8ff3149660df468d9359fbab80b4db33
出典データセット
uspto-grants-2014_07
特許番号
US08785462B2

反応ノート

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