Ethyl 2-(4-phenylcyclohexylidene)acetate → HCID 178471766, compound

HRID 220135Notes

Reaction equation

HRID 220135 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:1]1([C@H:7]2[CH2:8][CH2:9][C@H:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 11791415Ethyl 2-(4-phenylcyclohexylidene)acetate

Product 1

HCID 178471766HCID 178471766, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product of Example 1A (6.00 g, 24.7 mmol) was dissolved in 60 mL of ethanol and 10% Pd/C was added (600 mg). The reaction mixture was placed in a Par shaker at 60 psi for 2 h. After this time, the catalyst was filtered, and the solvents evaporated to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.05-1.22 (m, 2 H), 1.22-1.30 (m, 3 H), 1.43-1.59 (m, 2 H), 1.64-1.75 (m, 2 H), 1.86-1.96 (m, 3 H), 2.24 (d, J=6.44 Hz, 2 H), 2.40-2.49 (m, 1 H), 4.15 (q, J=7.35 Hz, 2 H), 7.17-7.23 (m, 3 H), 7.24-7.33 (m, 2 H); MS (ESI) m/z 247 [M+H]+.

Workup

  1. filtrationAfter this time, the catalyst was filtered
  2. customthe solvents evaporated

Sources & evidence

ORD record
ord-2eed8d5f3d774658a667c24ca1aa9878
Source dataset
uspto-grants-2012_06
Patent number
US08202878B2

Reaction notes

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