Dimethylformamide dimethyl acetal → 3-(Dimethylamino)-2-(furan-2-carbonyl)acrylonitrile
Reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[O:9]=[C:10]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)[CH2:11][C:12]#[N:13]>>[CH3:6][N:4]([CH:3]=[C:11]([C:10](=[O:9])[C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)[C:12]#[N:13])[CH3:5]Participants
3
Procedure
A 50 ml portion of dimethylformamide dimethylacetal was added to 25 g of solid β-oxo-2-furanepropanenitrile. This exothermic reaction produced yellow crystals. After one hour the volatiles were removed under reduced pressure and the residue was dissolved in methylene chloride. This solution was passed through a short pad of hydrous magnesium silicate. The eluate was refluxed with the gradual addition of hexane to the point of turbidity. Cooling and filtration gave 35.2 g of the desired compound, mp 117°-125° C.
Workup
- customThis exothermic reaction
- customproduced yellow crystals
- customAfter one hour the volatiles were removed under reduced pressure
- dissolutionthe residue was dissolved in methylene chloride
- temperatureThe eluate was refluxed with the gradual addition of hexane to the point of turbidity
- temperatureCooling
- filtrationfiltration
Sources & evidence
- ORD record
- ord-d828157c2500496682d5c7adfb8946f8
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04980472
Reaction notes
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