Furan → HCID 15346107, compound

HRID 567117Notes

Reaction equation

HRID 567117 reaction equation
C([Li])CCC.[O:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[CH3:11][C:12]1[CH:32]=[CH:31][CH:30]=[CH:29][C:13]=1[O:14][CH2:15][C:16]1[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=1[C:18](N1CCCC1)=[O:19]>C(OCC)C>[CH3:11][C:12]1[CH:32]=[CH:31][CH:30]=[CH:29][C:13]=1[O:14][CH2:15][C:16]1[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=1[C:18]([C:7]1[O:6][CH:10]=[CH:9][CH:8]=1)=[O:19]

Participants

5

Reactant 3

HCID 8029FuranHCID 21264588HCID 21264588, compoundHCID 178418339Butyllithium

Product 1

HCID 15346107HCID 15346107, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-20 °C

Procedure

27.8 g (0.1 mol) of 23% pure n-butyllithium are added dropwise within 15 minutes to a solution of 6.8 g (0.1 mol) of furan in 100 ml of diethyl ether which had been cooled to −20° C. The mixture was stirred at 20° C. for 2 hours, cooled once more to −20° C., and 14.8 g (0.05 mol) of N-[2-(2-methylphenoxymethyl)-benzoy]-pyrrolidine dissolved in 100 ml of diethyl ether are added dropwise within 15 minutes. After complete conversion (DC control), the mixture is poured into 300 ml of ice-cold ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. 13.1 g (89.7% of theory) of 2-[2-(2-methylphenoxymethyl)-benzoyl]-furan are obtained.

Workup

  1. temperaturecooled once more to −20° C.
  2. additionare added dropwise within 15 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3aff27d02814021986646eb68d11e15
Source dataset
uspto-grants-2001_01
Patent number
US06177459B1

Reaction notes

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