Acrylonitrile → HCID 18766626, compound

HRID 480719Notes

Reaction equation

HRID 480719 reaction equation
C1N2CCN(CC2)C1.[C:9](#[N:12])[CH:10]=[CH2:11].[O:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C[CH2:19][O:20][CH2:21][CH3:22]>>[C:9]([C:10]1[CH2:19][O:20][C:21]2[CH:22]=[C:14]([OH:13])[CH:15]=[CH:16][C:17]=2[CH:11]=1)#[N:12]

Participants

4

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 21868444Ether tetrahydrofuran

Product 1

HCID 18766626HCID 18766626, compound

Conditions

Temperature
80 °C

Procedure

A portion of the above mixture (30 g). was combined with 1,4-diazobicyclo[2.2.2]octane (Aldrich, 3.1 g, 27.7 mmol) and acrylonitrile (20 mL, 304 mmol) and heated at 80° C. for 4 h. The reaction mixture was concentrated in vacuo leaving an oily residue which was dissolved in a tetrahydrofuran/ether mixture (1:1), washed with 10% NaHCO3 (3×100 mL), dried (Na2SO4), and concentrated in vacuo to provide a crude mixture (36.1 g). The separated NaHCO3 layer was extracted with EtOAc (3×50 mL). The combined EtOAc layers were dried (Na2SO4) and concentrated in vacuo to yield 3-cyano-7-hydroxy-2H-1-benzopyran (3.2 g) which was ˜98% pure by 1H NMR.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customleaving an oily residue which
  3. washwashed with 10% NaHCO3 (3×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto provide a crude mixture (36.1 g)
  7. extractionThe separated NaHCO3 layer was extracted with EtOAc (3×50 mL)
  8. dry with materialThe combined EtOAc layers were dried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98d5e69a2d8d4840b6fce616611e1e85
Source dataset
uspto-grants-2003_11
Patent number
US06653340B1

Reaction notes

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