Acetone → 2-Bromo-1-thiophen-3-yl-butan-1-one

HRID 1677342

反応式

HRID 1677342 の反応式
CC[Mg+].[Br-].C[C:6]([OH:9])(C)C.[CH3:10][C:11]([CH3:13])=[O:12].[Br:14][CH:15]([CH2:23][CH3:24])[C:16]([C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)=[O:17]>C1C=CC=CC=1>[Br:14][CH:15]([CH2:23][CH3:24])[C:16]([C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)=[O:17].[S:20]1[CH:21]=[CH:22][C:18]([CH:16]([CH2:15][CH3:23])[C:6](=[O:9])[CH2:10][C:11](=[O:12])[CH3:13])=[CH:19]1

参加物

7

反応物 4

HCID 180Acetone2 回HCID 6386tert-ButanolHCID 595986182-Bromo-1-thiophen-3-yl-butan-1-oneHCID 178461630HCID 178461630、化合物

生成物 2

HCID 595986182-Bromo-1-thiophen-3-yl-butan-1-oneHCID 595986385-Thiophen-3-yl-heptane-2,4-dione

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

反応条件

温度
0 °C

実験手順

EtMgBr (6.69 ml, 13 mmol, 2 M in ethyl ether) in benzene (10 ml) was cooled to zero degrees C., and tBuOH (1.28 ml, 13 mmol) was slowly added. The reaction mixture was stirred at zero degrees C. for 5 minutes, then acetone (530 ul, 7 mmol) was added, followed by a solution of 2-Bromo-1-thiophen-3-yl-butan-1-one (1.3 g, 6 mmol) in 3 ml benzene via cannula. The reaction mixture was heated to reflux for 1 hour, and acetone (250 ul) was added. The reaction mixture was heated 2 hours more at reflux. The reaction was cooled, quenched with 1 N HCl (10 ml), extracted three times with diethyl ether, washed brine, and dried over magnesium sulfate. The solvent was removed in vacuo and the residue chromatographed (5% ethyl acetate/hexanes) to give 247 mg of 2-Bromo-1-thiophen-3-yl-butan-1-one starting material and 520 mg of 5-Thiophen-3-yl-heptane-2,4-dione, 44%.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe reaction mixture was heated 2 hours more
  4. temperatureat reflux
  5. temperatureThe reaction was cooled
  6. customquenched with 1 N HCl (10 ml)
  7. extractionextracted three times with diethyl ether
  8. washwashed brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was removed in vacuo
  11. customthe residue chromatographed (5% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-2bc1373aa4cf4991a1cbb14e81d7f24a
出典データセット
uspto-grants-2011_08
特許番号
US08008313B2

関連ノート

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