Ethyl Acetate → 5-(2-Trifluoromethyl-benzyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 2218666Notes

Reaction equation

HRID 2218666 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[CH:5]=[C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2.C(OCC)(=O)C.[H][H]>C(O)C.[Pd]>[F:1][C:2]([F:25])([F:26])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[CH2:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 597700785-(2-Trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 178418361HCID 178418361, compound

Product 1

HCID 597701195-(2-Trifluoromethyl-benzyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add 5-(2-trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (0.16 g, 0.45 mmol) to a mixture of 10% Pd/C (0.075 g) suspended in absolute ethanol (4.0 mL) and ethyl acetate (2.0 mL) and hydrogenate under a balloon of hydrogen at room temperature and pressure. Stir for 17 h, remove the catalyst via filtration through a pad of Celite. Evaporate the filtrate and pass through a plug of silica gel equilibrated with hexanes. Concentrated the filtrate to give the title product. MS (m/e): 352 (M+). Analysis for C23H19F3: Calcd: C, 78.39 H, 5.43. Found: C, 78.84 H, 5.11.

Workup

  1. customat room temperature
  2. customremove the catalyst
  3. filtrationvia filtration through a pad of Celite
  4. customEvaporate the filtrate and pass through a plug of silica gel
  5. concentrationConcentrated the filtrate

Sources & evidence

ORD record
ord-e93786ac722b46848f0733e1d9d0d150
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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