Benzophenone → 3,3-Diphenylacrylonitrile

HRID 2190323

반응식

HRID 2190323 반응식
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[C:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:15]1([C:14]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:5][C:3]#[N:4])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 3102BenzophenoneHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

생성물 1

HCID 2743523,3-Diphenylacrylonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of sodium hydride (60% wt in mineral oil) (0.780 g, 32.5 mmol) in THF (100 mL) at room temperature was added diethyl cyanomethylphosphonate (4.50 g, 25.4 mmol) (4 mL). The mixture was stirred for 30 min and benzophenone (4.22 g, 23.2 mmol) was added. The reaction mixture was stirred at room temperature for 1d, and partially concentrated, diluted with Et2O, washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 5% to 20% EtOAc in hexanes) gave 3,3-diphenylacrylonitrile.

후처리

  1. concentrationpartially concentrated
  2. additiondiluted with Et2O
  3. washwashed with water (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (eluted with 5% to 20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-2db76fdc3678418482438b285bd433dd
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324396B2

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