Ethyl Acetate → HCID 59770145, compound

HRID 2218668Notes

Reaction equation

HRID 2218668 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][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:25])([F:26])[C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][CH: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

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 59770205HCID 59770205, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59770145HCID 59770145, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add 5-(3-trifluoromethyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (0.145 g, 0.41 mmol), to a mixture of 10% Pd/C (0.04 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. Concentrated the filtrate to give the title product. MS (m/e): 352 (M+); GC retention time=7.11 min.

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-32b05bc68cf8403e8d2f94aed8fd1716
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

Loading…