Hydrochloric Acid → 1-(4-Bromophenyl)-3-(furan-2-yl)prop-2-en-1-one

HRID 1851320ノート

反応式

HRID 1851320 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=O.CO[Na].Cl>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH:9]=[CH:16][C:12]2[O:11][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7362FurfuralHCID 7466p-BromoacetophenoneHCID 178418582HCID 178418582、化合物

生成物 1

HCID 31238431-(4-Bromophenyl)-3-(furan-2-yl)prop-2-en-1-one収率 65%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 4-bromophenylethanone (112.6 g, 570 mmol) and furan-2-carbaldehyde (58.5 g, 610 mmol) in methanol (1.5 L) was added CH3ONa (31 g, 570 mmol) over 10 min and the reaction solution was stirred at room temperature overnight. The reaction mixture was neutralized with conc. HCl to pH=7, and the solvent was removed under reduced pressure. To the resultant residue was added EA and water. The aqueous layer was extracted with EA for 3 times. The combined layers were washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (PE (petroleum ether): EA (ethyl acetate)=10:1) to afford 1-(4-bromophenyl)-3-(furan-2-yl)prop-2-en-1-one (5A) as a yellow solid (90.2 g, 65%).

後処理

  1. customthe solvent was removed under reduced pressure
  2. additionTo the resultant residue was added EA and water
  3. extractionThe aqueous layer was extracted with EA for 3 times
  4. washThe combined layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (PE (petroleum ether): EA (ethyl acetate)=10:1)

出典と根拠

ORDレコード
ord-8e3be2129d174b409f4c49e020e60631
出典データセット
uspto-grants-2015_02
特許番号
US08957105B2

反応ノート

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