Ethyl Acetate → 5-(3,5-Bis-Trifluoromethyl-benzyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

HRID 2218672Notes

Reaction equation

HRID 2218672 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH:6]=[C:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][CH2:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2.C(OCC)(=O)C.[H][H]>C(O)C.[Pd]>[F:1][C:2]([F:29])([F:30])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:24]=1)[CH2:6][CH:7]1[C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 866039815-(3,5-Bis-trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 178418361HCID 178418361, compound

Product 1

HCID 866039825-(3,5-Bis-Trifluoromethyl-benzyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add 5-(3,5-bis-trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo [a,d]cycloheptene (0.28 g, 0.67 mmol) to a mixture of 10% Pd/C (0.08 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 give the title product. MS (m/e): 420 (M+); Analysis for C24H18F6: Calcd: C, 68.56 H, 4.31. Found: C, 68.55 H. 4.01.

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-9fc86eca8a2c4b309b707626a9dec8c4
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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