4-(2-Tert-butoxycarbonyl-vinyl)-3,5-dimethyl-benzoic acid methyl ester → 4-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid methyl ester

HRID 2047294Notes

Reaction equation

HRID 2047294 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([CH:11]=[CH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:6]([CH3:20])[CH:5]=1>C(O)C.C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[C:6]([CH3:20])[CH:5]=1

Participants

5

Reactant 1

HCID 669354604-(2-Tert-butoxycarbonyl-vinyl)-3,5-dimethyl-benzoic acid methyl ester

Product 1

HCID 669361734-(2-Tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid methyl esterYield 95.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-tert-butoxycarbonyl-vinyl)-3,5-dimethyl-benzoic acid methyl ester (11.2 g, 38.6 mmol) in ethanol (50 mL) and THF (50 mL), Pd/C (1.0 g, 10% Pd) is added. The mixture is stirred for 16 h at rt under 2.5 bar of H2. The catalyst is filtered off and the filtrate is concentrated and dried under HV to give 4-(2-tert-butoxycarbonyl-ethyl)-3,5-dimethyl-benzoic acid methyl ester (10.8 g) as a colourless oil; LC-MS: tR=1.08 min.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customdried under HV

Sources & evidence

ORD record
ord-a06c93bfbf464f17a7cd71e7771c6480
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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