4-(2-Tert-butoxycarbonyl-vinyl)-3-ethyl-5-methyl-benzoic acid benzyl ester → 4-(2-Tert-butoxycarbonylethyl)-3-ethyl-5-methylbenzoic acid

HRID 2040803Notes

Reaction equation

HRID 2040803 reaction equation
C([O:8][C:9](=[O:28])[C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([CH:17]=[CH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:12]([CH2:26][CH3:27])[CH:11]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[C:22]([O:21][C:19]([CH2:18][CH2:17][C:13]1[C:14]([CH3:16])=[CH:15][C:10]([C:9]([OH:28])=[O:8])=[CH:11][C:12]=1[CH2:26][CH3:27])=[O:20])([CH3:23])([CH3:25])[CH3:24]

Participants

4

Reactant 1

HCID 685558774-(2-Tert-butoxycarbonyl-vinyl)-3-ethyl-5-methyl-benzoic acid benzyl ester

Product 1

HCID 685516044-(2-Tert-butoxycarbonylethyl)-3-ethyl-5-methylbenzoic acidYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-tert-butoxycarbonyl-vinyl)-3-ethyl-5-methyl-benzoic acid benzyl ester (10.0 g, 26 mmol) in THF 100 mL), Pd/C (0.5 g, 20% Pd) is added under nitrogen. The mixture is stirred at rt for 48 h under 1 bar of H2. The catalyst is filtered off over a celite pad and the filtrate is concentrated to dryness to give 4-(2-tert-butoxycarbonyl-ethyl)-3-ethyl-5-methyl-benzoic acid (7.64 g) as a white solid; 1H NMR δ 1.29 (t, J=7.5 Hz, 3 H), 1.49 (s, 9 H), 2.36-2.41 (m, 2 H), 2.74 (q, J=7.5 Hz, 2 H), 2.99-3.05 (m, 2 H), 7.77 (s, 1 H), 7.80 (s, 1 H).

Workup

  1. filtrationThe catalyst is filtered off over a celite pad
  2. concentrationthe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-0e3eb1ea1507425ebe107477227ffb1e
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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