HCID 21955666, compound → HCID 69632622, compound

HRID 2213348Notes

Reaction equation

HRID 2213348 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][O:12][C:11](=[O:14])[C:10]=2[CH3:15])[CH:5]=[CH:6][C:7]=1[F:8]>CO>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][O:12][C:11](=[O:14])[C@H:10]2[CH3:15])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 1

HCID 21955666HCID 21955666, compound

Product 1

HCID 69632622HCID 69632622, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3,4-Difluorophenyl)-3-methyl-2(5H)-furanone (235 mg, 1.1 mmol.) was dissolved in methanol (20 ml) in a thick-walled flask and degassed by nitrogen bubbling. Palladium on charcoal (10%, 300 mg) was added and the flask shaken under an atmosphere of hydrogen at 40 psi on a Parr hydrogenator for 72 hours. The reaction was placed under nitrogen and filtered through a pad of Celite® washing well with methanol and the combined washings evaporated to afford the desired cis-dihydro-4-(3,4-difluorophenyl)-3-methyl-2(3H)-furanone as an oil (230 mg).

Workup

  1. customdegassed by nitrogen bubbling
  2. additionPalladium on charcoal (10%, 300 mg) was added
  3. filtrationfiltered through a pad of Celite®
  4. washwashing well with methanol
  5. customthe combined washings evaporated

Sources & evidence

ORD record
ord-06b3056d58614cdd9a927fbcae5d1cd3
Source dataset
uspto-grants-2006_09
Patent number
US07105509B2

Reaction notes

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