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

HRID 2218664Notes

Reaction equation

HRID 2218664 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=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]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][CH:6]1[C:7]2[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=2[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 597704015-(3-Methyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 178418361HCID 178418361, compound

Product 1

HCID 597698745-(3-Methyl-benzyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add 5-(3-methyl-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (0.18 g, 0.61 mmol), to a mixture of 10% Pd/C (0.045 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): 298 (M+). HPLC (ISO80-10M) t=1.00 (98%).

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-11b9c40f2a87473bb24e78c5d3a2f6bf
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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