Acrylonitrile → 6-Trifluoromethoxy-2H-chromene-3-carbonitrile

HRID 1697457

반응식

HRID 1697457 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH:4]=O.[C:15](#[N:18])[CH:16]=[CH2:17].C1N2CCN(CC2)C1>CCOCC>[F:12][C:11]([F:14])([F:13])[O:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[O:1][CH2:17][C:16]([C:15]#[N:18])=[CH:4]2

참가 물질

5

반응물 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehyde

생성물 1

HCID 669452446-Trifluoromethoxy-2H-chromene-3-carbonitrile수율 49.8%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
130 °C

실험 절차

To a microwave tube was added 2-hydroxy-5-trifluoromethoxybenzaldehyde (1 g, 5.0 mmol), 2-propenenitrile (1.6 mL, 24.3 mmol) and triethylenediamine (136 mg, 1.2 mmol). The reaction was heated in the microwave at 130° C. for 1 hour. After cooling, the resulting solution was diluted with ether (100 mL) and washed with 1N NaOH (50 mL), 1N HCl (50 mL) and brine (50 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (0 to 15% EtOAc in hexanes over 1 hour) gave the product (600 mg) as a solid. m/z=242.4 (M+1), r.t.=3.72 mins. 1H NMR (400 MHz; CDCl3) δ 7.14-7.12 (2H, m), 7.00 (1H, s), 6.89 (1H, d), 4.85 (2H, s).

후처리

  1. temperatureAfter cooling
  2. washwashed with 1N NaOH (50 mL), 1N HCl (50 mL) and brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9b24365928e2465c918785947e07515b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163901B2

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