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

HRID 426166

반응식

HRID 426166 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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))

출처 및 근거

ORD 기록
ord-54ef9bf61005419483207af4c5d88c10
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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