Ethyl Acetate → 5-(4-Trifluoromethyl-benzyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 2218670Notes

Reaction equation

HRID 2218670 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][C:6]([CH:7]=[C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)=[CH:5][CH:4]=1.C(OCC)(=O)C.[H][H]>C(O)C.[Pd]>[F:1][C:2]([F:25])([F:26])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[C:9]3[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=3[CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]2=3)=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 689355765-(4-Trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 178418361HCID 178418361, compound

Product 1

HCID 692731345-(4-Trifluoromethyl-benzyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add the 5-(4-trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (0.14 g, 0.45 mmol), to a mixture of 10% Pd/C (0.05 g) suspended in absolute ethanol (4.0 mL) and ethyl acetate (4.0 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. Concentrate the filtrate to gives the title product. MS (m/e): 352 (M+); Analysis for C23H19F3: Calcd: C, 78.39 H, 5.43. Found: C, 78.70 H, 5.16.

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. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-ea684c5ddae04c1f9849999141895d78
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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