Sodium Acetate → HCID 13851038, compound

HRID 986758Notes

Reaction equation

HRID 986758 reaction equation
Br[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]=[C:11]([C:14]#[N:15])[C:10](=[O:16])[C:9]=2[CH:17]=1)([CH3:4])[CH3:3].C([O-])(=O)C.[Na+]>CN(C)C=O>[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]=[C:11]([C:14]#[N:15])[C:10](=[O:16])[C:9]=2[CH:17]=1)([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 13728613HCID 13728613, compound

Product 1

HCID 13851038HCID 13851038, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(1-bromo-1-methylethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile (2.0 g), sodium acetate (575 mg) and dimethylformamide (20 ml) was heated for one hour, which was then concentrated. The concentrate was dissolved in chloroform. The solution was washed with water and dried (sodium sulfate), followed by removing chloroform by evaporation. The residue was subjected to a silica-gel (100 g) column chromatography, eluting with chloroform-acetone-formic acid (20:1:0.1). The initial eluate was recrystallized from ethanol to give colorless crystals (1.07 g) of 6-isopropenyl-4-oxo-4H-1-benzopyran-3-carbonitrile, m.p. 142°-144° C.

Workup

  1. temperaturewas heated for one hour
  2. concentrationwhich was then concentrated
  3. dissolutionThe concentrate was dissolved in chloroform
  4. washThe solution was washed with water
  5. dry with materialdried (sodium sulfate)
  6. customby removing chloroform
  7. customby evaporation
  8. washeluting with chloroform-acetone-formic acid (20:1:0.1)
  9. customThe initial eluate was recrystallized from ethanol

Sources & evidence

ORD record
ord-bb98bd0593a649ec83d5ed9a4756de6a
Source dataset
uspto-grants-1987_12
Patent number
US04716167

Reaction notes

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