Ethyl 4-phenylbicyclo[2.2.2]oct-2-ene-1-carboxylate → Ethyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate

HRID 908109Notes

Reaction equation

HRID 908109 reaction equation
[C:1]1([C:7]23[CH2:14][CH2:13][C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])([CH2:11][CH2:12]2)[CH:9]=[CH:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.[Pt]>[C:1]1([C:7]23[CH2:12][CH2:11][C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])([CH2:9][CH2:8]2)[CH2:13][CH2:14]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 25257890Ethyl 4-phenylbicyclo[2.2.2]oct-2-ene-1-carboxylate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 21627803Ethyl 4-phenylbicyclo[2.2.2]octane-1-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 4-phenylbicyclo[2.2.2]oct-2-ene-1-carboxylate (Intermediate 3; 26.3 g, 102.5 mmol) in absolute ethanol (600 mL) and 10% Pt on carbon (2.4 mg) were stirred under a balloon of hydrogen at ambient temperature overnight. The reaction mixture was filtered and the solvent removed under reduced pressure to leave a colourless oil which rapidly formed a white solid (22.179 g, 85.96 mmol, 84%) 1H NMR (CDCl3) δ 1.25 (3H, t), 1.83-1.96 (12H, m), 4.12 (2H, q), 7.15-7.20 (1H, m), 7.28-7.31 (4H, m); GC-MS EI m/e M+ 258.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed under reduced pressure
  3. customto leave a colourless oil which

Sources & evidence

ORD record
ord-05f650b9b57948879f796025e17f3d98
Source dataset
uspto-grants-2011_09
Patent number
US08017603B2

Reaction notes

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