Chloroform → Methyl 4-{[2-oxodihydro-3(2H)-furanylidene]methyl}benzoate

HRID 2243286Notes

Reaction equation

HRID 2243286 reaction equation
C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:8]2[CH2:12][CH2:11][O:10][C:9]2=[O:13])C=CC=CC=1.[CH:26]([C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)=O.C(Cl)(Cl)Cl>CS(C)=O>[O:13]=[C:9]1[C:8](=[CH:26][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=2)[CH2:12][CH2:11][O:10]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 15294Methyl 4-FormylbenzoateHCID 971112(3H)-Furanone, 3-(triphenylphosphoranylidene)-

Product 1

HCID 68707654Methyl 4-{[2-oxodihydro-3(2H)-furanylidene]methyl}benzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 40.00 g (0.12 mol) of 3-(triphenylphosphoranylidene)dihydro-2(3H)-furanone and 20.85 g (0.13 mol) of methyl 4-formylbenzoate in 240 ml of dimethyl sulfoxide is stirred at 80° C. for 18 hours. After cooling, 400 ml of chloroform are added, and the mixture is extracted five times with 200 ml of water. The organic phase is dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The residue is stirred with diethyl ether and dried under reduced pressure at 40° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted five times with 200 ml of water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. stirringThe residue is stirred with diethyl ether
  6. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-589c9b94c9d14b80be1d75ac0fa7a000
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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