Ethyl Acetate → HCID 59770290, compound

HRID 2218662Notes

Reaction equation

HRID 2218662 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.C(OCC)(=O)C.[H][H]>C(O)C.[Pd]>[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][CH:5]1[C:6]2[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=2[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 59769953HCID 59769953, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59770290HCID 59770290, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add the 5-(2-methyl-benzylidene)-10,11-dihydro-5H-dibenzo [a,d]cycloheptene (0.19 g, 0.64 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. Concentrate the filtrate to give the title product: MS (m/e) 298 (M+). Analysis for C23H22: Calcd: C, 91.99 H, 7.39. Found: C, 91.95 H, 7.39.

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-bf8ca9bbe1b94454abf528637061c4eb
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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