2-(2,5-Dimethoxy-phenyl)-cyclopent-1-enecarboxylic acid ethyl ester → 2-(2,5-Dimethoxy-phenyl)-cyclopentanecarboxylic acid ethyl ester

HRID 418921Notes

Reaction equation

HRID 418921 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[O:19][CH3:20])=[O:5])[CH3:2]>CO.C(=O)(O)[O-].[Na+].[Pt]=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[O:19][CH3:20])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 121253312-(2,5-Dimethoxy-phenyl)-cyclopent-1-enecarboxylic acid ethyl ester

Product 1

HCID 666519992-(2,5-Dimethoxy-phenyl)-cyclopentanecarboxylic acid ethyl esterYield 89.8%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Dissolve 2-(2,5-dimethoxy-phenyl)-cyclopent-1-enecarboxylic acid ethyl ester (5 g, 18 mmol) in methanol (150 ml) exchange with N2 3×, add platinum oxide (1.6 g 7.2 mmol), add 60 psi of H2 for 24 hours at room temperature. Filter off catalyst, concentrate the filtrate to give the title compound (4.5 g, 89%): 1H NMR (CDCl3) δ 6.77-6.67 (m, 3H), 3.81 (s, 3H), 3.74 (s, 3H), 3.71-3.57 (m, 3H), 3.32-3.27 (m, 1H), 2.13-1.96 (m, 4H), 1.89-1.83 (m, 1H), 1.70-1.62 (m, 1H), 0.83-0.79 (t, 3H).

Workup

  1. additionadd 60 psi of H2 for 24 hours at room temperature
  2. filtrationFilter off catalyst
  3. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-267dbae1798f4b0eb8b9194934d9e8ad
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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