Acrylonitrile → 6-fluoro-2,3-dihydro-4-cyano-4-[(trimethylsilyl)oxy]-4H-benzopyran

HRID 487201

반응식

HRID 487201 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][C:7](=[O:11])[C:6]=2[CH:12]=1.FC1C=CC(O)=CC=1.[C:21](#[N:24])C=C.[CH3:25][Si:26](C#N)([CH3:28])[CH3:27]>C(Cl)Cl.[I-].[Zn+2].[I-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][C:7]([C:21]#[N:24])([O:11][Si:26]([CH3:28])([CH3:27])[CH3:25])[C:6]=2[CH:12]=1

참가 물질

7

반응물 4

HCID 7855AcrylonitrileHCID 97324-FluorophenolHCID 82115Trimethylsilyl cyanideHCID 27332626-fluoro-2,3-dihydro-4H-1-benzopyran-4-one

생성물 1

HCID 143394296-fluoro-2,3-dihydro-4-cyano-4-[(trimethylsilyl)oxy]-4H-benzopyran

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 20 g (0.12 moles) of 2,3,-dihydro-6-fluoro-4H-benzopyran-4-one (prepared from 4-fluorophenol and acrylonitrile as described in J. Med. Chem., 28, 1716 (1985) and 23 mL (0.18 moles) of trimethylsilyl cyanide in 220 mL of CH2Cl2 was added 500 mg of zinc iodide. The reaction was stirred at room temperature for 20 hours then poured onto ice-water. The CH2Cl2 layer was washed with water, 10% aqueous NaHCO3 and brine then dried over MgSO4, filtered and evaporated to give 32 g of crude product which was used without purification.

후처리

  1. additionthen poured onto ice-water
  2. washThe CH2Cl2 layer was washed with water, 10% aqueous NaHCO3 and brine
  3. dry with materialthen dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-70aed26fa3894f3d9b9329d82e6b201c
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05294635

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