Acetone → 3-(2-Methylpropenyl)benzonitrile

HRID 2080131

反応式

HRID 2080131 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=1)(=O)OCC)C.[CH3:20][C:21]([CH3:23])=O.O>O1CCCC1>[CH3:20][C:21]([CH3:23])=[CH:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[C:18]#[N:19]

参加物

6

反応物 4

HCID 180AcetoneHCID 962WaterHCID 24758Sodium hydrideHCID 21466817Phosphonic acid, [(3-cyanophenyl)methyl]-, diethyl ester

生成物 1

HCID 190247923-(2-Methylpropenyl)benzonitrile収率 28%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (0.40 g, 10 mmol, 60% in oil) was suspended in tetrahydrofuran (5 mL), (3-cyanobenzyl)phosphonic acid diethyl ester obtained in Preparation Example 135 (2.53 g, 10 mmol) was added dropwise under stirring at room temperature. After stirring for 1 hour at 60° C., the solution was allowed to room temperature, acetone (0.92 g, 20 mmol) was added dropwise, and the solution was further stirred for 30 minutes at room temperature. Water (100 mL) was added to the reaction solution, which was then extracted with ethyl acetate (50 mL). The organic layer was washed with water, then, dried over anhydrous magnesium sulfate, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3), and the title compound (0.44 g, 2.80 mmol, 28%) was obtained as a colorless oil.

後処理

  1. additionwas added dropwise
  2. stirringAfter stirring for 1 hour at 60° C.
  3. customwas allowed to room temperature
  4. stirringthe solution was further stirred for 30 minutes at room temperature
  5. extractionwas then extracted with ethyl acetate (50 mL)
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=97:3)

出典と根拠

ORDレコード
ord-a8196efd69584778a5d29d58fef1f55d
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

関連ノート

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