Acrylonitrile → 9-methoxy-3H-benzo[f]chromene-2-carbonitrile

HRID 394650Notes

Reaction equation

HRID 394650 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[C:3]=1[CH:14]=O.[C:16](#[N:19])[CH:17]=[CH2:18].N12CCN(CC1)CC2>C(OCC)(=O)C>[CH3:13][O:12][C:6]1[CH:7]=[CH:8][C:9]2[CH:10]=[CH:11][C:2]3[O:1][CH2:18][C:17]([C:16]#[N:19])=[CH:14][C:3]=3[C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 105360972-Hydroxy-7-methoxy-1-naphthaldehyde

Product 1

HCID 181774259-methoxy-3H-benzo[f]chromene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under an anhydrous atmosphere, the aldehyde obtained in Step C (2 g: 9.9 mmol) is partially solubilised in acrylonitrile (6.5 ml:49.4 mmol:10 eq.). The solution becomes clear after the addition of 1,4-diazabicyclo[2.2.2]octane (227 mg:2.47 mmol:0.25 eq.) and becomes a red colour when heated at reflux for a period of 18 hours. The reaction medium is then diluted with ethyl acetate and washed in succession with a 1N sodium hydroxide solution (20 ml) and then a 1N hydrochloric acid solution (20 ml). The concentrated organic phases are purified on a flash silica column eluted with an AcOEt/PE mixture (0.1/1).

Workup

  1. temperatureheated
  2. temperatureat reflux for a period of 18 hours
  3. washwashed in succession with a 1N sodium hydroxide solution (20 ml)
  4. customThe concentrated organic phases are purified on a flash silica column
  5. washeluted with an AcOEt/PE mixture (0.1/1)

Sources & evidence

ORD record
ord-e6337fdc95b2439c8cf793e66d0f8e2b
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

Loading…