Dimethylformamide → 2-Formyl-3-methyl-5-(4-methylphenyl)furan

HRID 22245Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[O:14][CH:13]=1.[OH-].[Na+]>ClC(Cl)C>[CH:8]([C:13]1[O:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:16][C:12]=1[CH3:11])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Phosphorus oxychloride (12 ml) was added slowly to dimethylformamide (9.85 ml) with stirring at 0° C., and the mixture stirred at 0° C. for 30 minutes. A solution of 3-methyl-5-(4-methylphenyl)furan (22 g) in 50 ml of dichloroethane was added dropwise over a period of 15 minutes, maintaining the temperature at 0° C. The mixture was then stirred at room temperature for 11/2 hours. Ice water was then added, and the pH of the aqueous layer adjusted to about 8 with dilute sodium hydroxide. The organic layer was separated, the aqueous layer extracted with dichloromethane, the organic portions combined and solvent removed under reduced pressure. The solvent was removed from the filtrate under reduced pressure, and the residue flash chromatographed on silica gel, eluting with 10% ethyl acetate in heptane, to yield 19.2 g of 2-formyl-3-methyl-5-(4-methylphenyl)furan.

Workup

stirringthe mixture stirred at 0° C. for 30 minutes
temperaturemaintaining the temperature at 0° C
stirringThe mixture was then stirred at room temperature for 11/2 hours
customThe organic layer was separated
extractionthe aqueous layer extracted with dichloromethane
customsolvent removed under reduced pressure
customThe solvent was removed from the filtrate under reduced pressure
customthe residue flash chromatographed on silica gel
washeluting with 10% ethyl acetate in heptane

Sources & evidence

ORD record: ord-1d5091b33d1b49e295010bdab9394b2a
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05428037

Reaction notes

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