Hydrochloric Acid → 2-(3,4-Dimethoxybenzoyl)furan

HRID 2420091Notes

Reaction equation

HRID 2420091 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:16]#N.Cl.CC[O:26]CC>O1CCCC1>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:16]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 8029FuranHCID 748423,4-DimethoxybenzonitrileHCID 178418339Butyllithium

Product 1

HCID 8383262-(3,4-Dimethoxybenzoyl)furan

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Freshly distilled furan (57 ml, 790 mmoles) in dry ether (500 ml) is cooled (5° C) under nitrogen and n-butyllithium (340 ml, 2.35M in hexane) is added dropwise to the stirred solution. The mixture is stirred for 3 days at room temperature. The mixture is cooled to -30° C and a solution of 3,4-dimethoxybenzonitrile (77.5 g, 480 mmoles, described in Example I) in ether (200 ml) is added dropwise to the mixture. The brown mixture is stirred for 5 hours at room temperature. Wet tetrahydrofuran is cautiously added and the mixture is poured on ice. Hydrochloric acid (3N) is added until the mixture is acidic. The mixture is extracted with ether. The aqueous phase is rendered basic and extracted with methylene chloride. The organic extract is washed with brine, dried and evaporated. The residue is subjected to chromatography on silica gel using chloroform and the eluates are evaporated to give the title compound, mp 112°-114° C.

Workup

  1. temperatureThe mixture is cooled to -30° C
  2. stirringThe brown mixture is stirred for 5 hours at room temperature
  3. additionthe mixture is poured on ice
  4. extractionThe mixture is extracted with ether
  5. extractionextracted with methylene chloride
  6. extractionThe organic extract
  7. washis washed with brine
  8. customdried
  9. customevaporated
  10. customthe eluates are evaporated

Sources & evidence

ORD record
ord-51475aaaf4e14ba9a05bd4f3a10377d6
Source dataset
uspto-grants-1978_08
Patent number
US04108997

Reaction notes

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