Acrylonitrile → 7-(phenylmethoxy)-2H-1-benzopyran-3-carbonitrile

HRID 2232492Notes

Reaction equation

HRID 2232492 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCN(CC1)CC2.[C:26](#[N:29])[CH:27]=[CH2:28]>>[C:2]1([CH2:1][O:8][C:9]2[CH:16]=[CH:15][C:12]3[CH:13]=[C:27]([C:26]#[N:29])[CH2:28][O:17][C:11]=3[CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Product 1

HCID 143297587-(phenylmethoxy)-2H-1-benzopyran-3-carbonitrileYield 45.7%

Procedure

A mixture of 1.14 g of 4-benzyloxy-2-hydroxybenzaldehyde, 0.125 g of 1,4-diazabicyclo[2,2,2]octane and 0.65 g of acrylonitrile was stirred and heated at 80°-85° C., under argon, for 2 hours. After removal of the solvent, the residual product was dissolved in tetrahydrofuran-ether (1:1), washed with 1N-sodium hydroxide, water, dried, and the solvents evaporated in vacuo. The crude material (1.10 g) was purified by column chromatography on silica gel to afford 0.6 g (45.7%) of 7-(phenylmethoxy)-2H-1-benzopyran-3-carbonitrile, as a colorless solid mp 95°-98° C. (from ethyl acetate-hexane).

Workup

  1. temperatureheated at 80°-85° C., under argon, for 2 hours
  2. customAfter removal of the solvent
  3. dissolutionthe residual product was dissolved in tetrahydrofuran-ether (1:1)
  4. washwashed with 1N-sodium hydroxide, water
  5. customdried
  6. customthe solvents evaporated in vacuo
  7. customThe crude material (1.10 g) was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f5580c6526764275a1dfb9444120dcbd
Source dataset
uspto-grants-1988_11
Patent number
US04788214

Reaction notes

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