Benzaldehyde, 3,5-dimethyl- → 3-(3,5-Dimethyl-phenyl)-acrylonitrile

HRID 426166

反応式

HRID 426166 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH:5]=O.[C:11]([CH2:13]P(=O)(OCC)OCC)#[N:12].CC(C)([O-])C.[K+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:13][C:11]#[N:12])[CH:7]=[C:8]([CH3:10])[CH:9]=1

参加物

5

反応物 3

HCID 34225Benzaldehyde, 3,5-dimethyl-HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 667054533-(3,5-Dimethyl-phenyl)-acrylonitrile収率 94.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred mixture of 3,5-dimethyl benzaldehyde (13.4 g, 0.1M), diethyl cyanomethylphosphonate (19.4 g, 0.11M) in anhydrous THF (200 ml) under nitrogen at 0° C. (ice bath), was added potassium t-butoxide (12.3 g, 0.11M). After stirring for 1 hr., the mixture was stirred for overnight at room temperature. The mixture was then partitioned between ether and water. The ether layer was taken, dried with anhydrous magnesium sulfate, filtered, evaporated in vacuo, and the residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:20)) to afford 14.8 g (86%) of a white solid. m.p. 67-68° C.; 1H NMR (200 MHz, CDCl3) δ 2.33 (6H, s), 5.83 (1H, d, J=16.6 Hz), 7.05 (3H, s), 7.28 (1H, d, J=16.6 Hz).

後処理

  1. stirring, the mixture was stirred for overnight at room temperature
  2. customThe mixture was then partitioned between ether and water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:20))

出典と根拠

ORDレコード
ord-54ef9bf61005419483207af4c5d88c10
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

関連ノート

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