Acrylonitrile → 6-fluoro-2H-chromene-3-carbonitrile

HRID 536467Notes

Reaction equation

HRID 536467 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.[C:11](#[N:14])[CH:12]=[CH2:13].C1N2CCN(CC2)C1>[OH-].[Na+]>[F:1][C:2]1[CH:9]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:10][CH2:13][C:12]([C:11]#[N:14])=[CH:7]2

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 27373285-Fluorosalicylaldehyde

Product 1

HCID 150274626-fluoro-2H-chromene-3-carbonitrileYield 288%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-fluoro-2-hydroxybenzaldehyde (1.00 g, 8.92 mmol) and acrylonitrile (9.40 mL, 143 mmol) was refluxed overnight with DABCO (1.00 g, 8.92 mmol). The mixture was cooled and 1 M NaOH (10 mL) was added. The mixture was extracted with EtOAc (20 mL), and the organic layer was dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes) to provide the title compound (4.50 g) as yellow crystals. 1H NMR (300 MHz, CDCl3) δ 7.13 (m, 1H), 6.98 (td, J=8.5, 3.0 Hz, 1H), 6.89-6.80 (m, 2H), 4.80 (d, J=1.4 Hz, 2H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with EtOAc (20 mL)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bed34000f890428ab403ba851563a5f1
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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