Boron trifluoride etherate → 2-(5-Phenyloxazol-2-yl)acetonitrile

HRID 1397370노트

반응식

HRID 1397370 반응식
B(F)(F)F.CCOCC.[C:10](#[N:14])[CH2:11][C:12]#[N:13].[N+](=[CH:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19])=[N-]>C(Cl)Cl>[C:20]1([C:18]2[O:19][C:12]([CH2:11][C:10]#[N:14])=[N:13][CH:17]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 8010MalononitrileHCID 18667Diazoacetophenone

생성물 1

HCID 126396202-(5-Phenyloxazol-2-yl)acetonitrile수율 32%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

BF3.Et2O (1.1 mL, 8.5 mmol) was added dropwise to a solution of malononitrile (2.26 g, 34.2 mmol) in dry CH2Cl2 (20 mL) at 0° C., followed by addition of 2-diazo-1-phenylethanone (0.5 g, 3.4 mmol) in DCM (5 mL). The reaction mixture was stirred at room temperature for 1 h and then quenched with aqueous 10% NaOH solution. The organic product was extracted with EtOAc and the combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 5-10% EtOAc in petroleum ether) to get 2-(5-phenyloxazol-2-yl)acetonitrile (200 mg, yield 32%) as a brown solid. 1H NMR (300 MHz, CDCl3) δ 7.66-7.63 (m, 2H), 7.47-7.38 (m, 3H), 7.32 (s, 1H), 4.02 (s, 2H). MS (ESI) m/z: Calculated for C11H8N2O: 184.06. found: 185.2 (M+H)+.

후처리

  1. customquenched with aqueous 10% NaOH solution
  2. extractionThe organic product was extracted with EtOAc
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 5-10% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-1f6b58abba0e4f67b18d629d9db5ad84
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

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