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

HRID 487201

Reaktionsgleichung

Reaktionsgleichung von HRID 487201
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9883512zinc(II)iodideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-70aed26fa3894f3d9b9329d82e6b201c
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294635

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