Ethyl Acetate → 3,4-diphenyl-5H-furan-2-one

HRID 929492Notes

Reaction equation

HRID 929492 reaction equation
[CH2:1]1[CH2:11][CH2:10]N2[C:4](=NCCC2)[CH2:3][CH2:2]1.[CH3:12][C:13](=[O:17])[O:14][CH2:15][CH3:16]>C(#N)C>[C:1]1([C:12]2[C:13](=[O:17])[O:14][CH2:15][C:16]=2[C:4]2[CH:3]=[CH:2][CH:1]=[CH:11][CH:10]=2)[CH:11]=[CH:10][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 3440493,4-diphenyl-5H-furan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After dissolving compound 2 (5.00 g, 36.7 mmol) in ACN (30 ml), compound 10 (7.31 g, 36.7 mmol) and TEA (5.63 ml) were sequentially added thereto. After the agitation for 30 minutes at room temperature, the temperature was reduced to 0° C., DBU (16.5 ml) was dropped and the agitation for 1 hour was carried out. After the termination of the reaction, EA and 1N HCL aqueous solution were added thereto and the organic layer was washed three times with brine. Water was removed by using anhydrous Na2SO4 and the distillation under the reduced pressure was carried out to obtain compound 18.

Workup

  1. additionwere sequentially added
  2. customwas reduced to 0° C.
  3. waitthe agitation for 1 hour was carried out
  4. additionwere added
  5. washthe organic layer was washed three times with brine
  6. customWater was removed
  7. distillationthe distillation under the reduced pressure

Sources & evidence

ORD record
ord-c7e96413a1bc4e30b3c9e41023d5aa43
Source dataset
uspto-grants-2016_03
Patent number
US09296690B2

Reaction notes

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