HCID 53688447, compound → HCID 18790086, compound

HRID 1107133Notes

Reaction equation

HRID 1107133 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 53688447HCID 53688447, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18790086HCID 18790086, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(3,4-dimethoxyphenyl)-7-phenyl-2-heptenoate (0.4 g, 1.1 mmol) in ethanol (20 mL) containing 10% Pd/C (few mg) is stirred under a balloon of hydrogen for 4 hours at room temperature. The catalyst is filtered and the solvent is removed in vacuo to produce ethyl 3-(3,4-dimethoxyphenyl)-7-phenylheptanoate (0.3 g, 73%) as an oil. 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.11-1.20 (t, 3H), 1.20-1.65 (m, 6H), 2.45-2.59 (m, 4H), 2.92-3.10 (m, 1H), 3.82 (s, 6H), 4.00-4.08 (q, 2H), 6.62-6.82 (m, 3H), 7.02-7.28 (m, 5H); MS (EI) m/e 370 (M+).

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e75085926b684c17959c60cad550a36d
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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