5-Benzyloxy-2-(2-tert-butoxycarbonyl-vinyl)-benzoic acid 2-trimethylsilanyl-ethyl ester → 2-(2-Tert-butoxycarbonyl-ethyl)-5-hydroxy-benzoic acid 2-trimethylsilanyl-ethyl ester

HRID 1181105Notes

Reaction equation

HRID 1181105 reaction equation
[CH3:1][Si:2]([CH3:32])([CH3:31])[CH2:3][CH2:4][O:5][C:6](=[O:30])[C:7]1[CH:12]=[C:11]([O:13]CC2C=CC=CC=2)[CH:10]=[CH:9][C:8]=1[CH:21]=[CH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[H][H]>CCO.[Pd]>[CH3:31][Si:2]([CH3:1])([CH3:32])[CH2:3][CH2:4][O:5][C:6](=[O:30])[C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24]

Participants

5

Reactant 2

HCID 692318995-Benzyloxy-2-(2-tert-butoxycarbonyl-vinyl)-benzoic acid 2-trimethylsilanyl-ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 589791782-(2-Tert-butoxycarbonyl-ethyl)-5-hydroxy-benzoic acid 2-trimethylsilanyl-ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5-benzyloxy-2-(2-tert-butoxycarbonyl-vinyl)-benzoic acid 2-trimethylsilanyl-ethyl ester (6.20 g, 13.6 mmol) in EtOH (95 mL) was treated with Pd/C (5%, 0.775 g). The resulting suspension was treated with hydrogen at 60 psi for 6 h at room temperature. The catalyst was filtered through a pad of Celite, and the filtrate was concentrated to an oil (4.30 g, 86%). 1H NMR (400 MHz, CDCl3): δ 0.07 (s, 9H), 0.96 (t, 1H, J=8.8 Hz), 1.12 (t, 1H, J=8.8 Hz), 1.40 (s, 9H), 2.52 (t, 1H, J=7.8 Hz), 3.13 (t, 1H, J=7.8 Hz), 3.73 (t, 1H, J=8.5 Hz), 4.36 (t, 1H, J=8.5 Hz), 5.00 (br s, 1H), 6.88 (dd, 1H, J=2.4, 8.3 Hz), 7.14 (d, 1H, J=8.3 Hz), 7.35 (d, 1H, J=2.4 Hz).

Workup

  1. filtrationThe catalyst was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated to an oil (4.30 g, 86%)

Sources & evidence

ORD record
ord-72933543c2f047b88473dc1b977727a3
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

Loading…