Acrylonitrile → 7-METHOXY-2H-CHROMENE-3-CARBONITRILE

HRID 1803750Notes

Reaction equation

HRID 1803750 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:12](#[N:15])[CH:13]=[CH2:14].N12CCN(CC1)CC2>[OH-].[Na+]>[CH3:11][O:10][C:8]1[CH:9]=[C:2]2[C:3]([CH:4]=[C:13]([C:12]#[N:15])[CH2:14][O:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 122430247-METHOXY-2H-CHROMENE-3-CARBONITRILE

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-Hydroxy-4-methoxybenzaldehyde (Aldrich, 5.0 g, 32.9 mmol), acrylonitrile (11 mL, 164 mmol), and 1,4-diazabicyclo[2.2.2]octane (0.92 g, 8.2 mmol) were heated in a microwave Personal Chemistry at 95° C. for 5 hours. Sodium hydroxide (200 mL) was added and the mixture was extracted with ethyl acetate (200 mL) and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Chromatography on silica gel eluting with 0-to-50% ethyl acetate in hexane afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.77 (s, 3H), 4.84 (d, J=1.36 Hz, 2H), 6.50 (d, J=2.71 Hz, 1H), 6.61 (dd, J=8.48, 2.71 Hz, 1H), 7.21 (d, J=8.48 Hz, 1H), 7.52 (s, 1H). MS (DCI) m/z 205.07 (M+NH4)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (200 mL) and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4c558b796b644a496f484ffe8f01b0a
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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