Hexane → alpha-Acetyl-4-phenylthiophenylacetonitrile

HRID 37130

反応式

HRID 37130 の反応式
[H-].[Na+].[C:3](OCC)(=[O:5])[CH3:4].[C:9]1([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCCCCC>O1CCCC1>[C:3]([CH:22]([C:19]1[CH:20]=[CH:21][C:16]([S:15][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:17][CH:18]=1)[C:23]#[N:24])(=[O:5])[CH3:4]

参加物

6

反応物 4

HCID 8058HexaneHCID 8857Ethyl Acetate2 回HCID 24758Sodium hydrideHCID 238605[4-(Phenylsulfanyl)phenyl]acetonitrile

生成物 1

HCID 54503700alpha-Acetyl-4-phenylthiophenylacetonitrile収率 73.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred suspension of 144 mg of 60% sodium hydride, in 10 ml of tetrahydrofuran at 0° C. under nitrogen atmosphere was added a mixture of 396 mg of ethyl acetate, 675 mg of 4-phenylthiophenylacetonitrile and 5 ml of tetrahydrofuran. Thirty minutes later, the ice bath was removed. Seventeen hours later, the tetrahydrofuran was distilled off in vacuo, and 10 ml of 2N hydrochloric acid and 20 ml of dichloromethane were added and separated, and the water layer was further extracted twice in 20 ml of dichloromethane. The organic layer and extract were combined, and dried by anhydrous magnesium sulfate, and concentrated in vacuo, and the residue was isolated and refined by silica gel chromatography (the eluent was a mixed solvent of hexane:ethyl acetate at a (v/v) rate of 4:1), and 587 mg of the title compound was obtained.

後処理

  1. customThirty minutes later, the ice bath was removed
  2. distillationSeventeen hours later, the tetrahydrofuran was distilled off in vacuo, and 10 ml of 2N hydrochloric acid and 20 ml of dichloromethane
  3. additionwere added
  4. customseparated
  5. extractionthe water layer was further extracted twice in 20 ml of dichloromethane
  6. extractionThe organic layer and extract
  7. dry with materialdried by anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customthe residue was isolated

出典と根拠

ORDレコード
ord-910d4692394c4911abb8f623d26d754d
出典データセット
uspto-grants-1995_05
特許番号
US05420128

関連ノート

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