HCID 68430673, compound → HCID 68430396, compound

HRID 2267008Notes

Reaction equation

HRID 2267008 reaction equation
C([O:8][C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[C:13]([O:19]CC2C=CC=CC=2)[CH:12]=[CH:11][C:10]=1[C:27](=[O:29])[CH3:28])C1C=CC=CC=1>C(O)C.C1CCCCC=1.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[C:14]([C:15]([F:16])([F:17])[F:18])=[C:13]([OH:19])[CH:12]=[CH:11][C:10]=1[C:27](=[O:29])[CH3:28]

Participants

5

Reactant 1

HCID 68430673HCID 68430673, compound

Product 1

HCID 68430396HCID 68430396, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

Add 20% palladium hydroxide on carbon (11.0 g, 15 mmol) to a solution of 1-(2,4-bis-benzyloxy-3-trifluoromethyl-phenyl)-ethanone (6.00 g, 15 mmol) in ethanol (75 mL) and cyclohexene (75 mL) and stir. Purge the reaction vessel with argon. Heat to reflux. After 18 hours, cool to ambient temperature, filter and concentrate under reduced pressure to yield the title compound as a grey solid (3.00 g, 91%): 1H NMR (CD3CN) δ 2.55 (s, 3H), 6.51 (d, 1H), 7.88 (d, 1H), 13.91 (bs, 1H).

Workup

  1. customPurge the reaction vessel with argon
  2. temperatureHeat to reflux
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-9e232fb378b94283a3b89feff563a7a6
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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