HCID 178471801, compound → HCID 178471800, compound

HRID 505273Notes

Reaction equation

HRID 505273 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([O:14]CC2C=CC=CC=2)=[O:13])[CH2:8][CH2:7]1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 1

HCID 178471801HCID 178471801, compound

Product 1

HCID 178471800HCID 178471800, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl trans-4-(2-ethoxy-2-oxoethyl)cyclohexanecarboxylate (52.4 g, 0.172 mol) in MeOH (500 mL) was added 10% Pd/C (5 g). The reaction was hydrogenated at 40 psi for 1 hour and then the catalyst was removed by filtration. The filtrate was concentrated to afford trans-4-(2-ethoxy-2-oxoethyl)cyclohexanecarboxylic acid. 1H NMR (CDCl3, 500 MHz) δ 4.12 (q, J=7.1 Hz, 2H), 2.24 (m, 1H), 2.19 (d, J=7.1 Hz, 2H), 1.98-2.04 (m, 2H), 1.81-1.87 (m, 2H), 1.77 (m, 1H), 1.46 (qd, J=13.0, 3.4 Hz, 2H), 1.24 (t, J=7.1 Hz, 3H), 1.02 (qd, J=13.0, 3.4 Hz, 2H).

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1167515a4bd24185a5ceff2e5fc63828
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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