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

HRID 2248281Notes

Reaction equation

HRID 2248281 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-15027083de1a4046b004c093d1deadb7
Source dataset
uspto-grants-1991_08
Patent number
US05039672

Reaction notes

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