(S)-2-allyloxy-3-(4-benzyloxy-phenyl)-propionic acid ethyl ester → (S)-3-(4-hydroxy-phenyl)-2-propoxy-propionic acid ethyl ester

HRID 459270Notes

Reaction equation

HRID 459270 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C@@H:5]([O:21][CH2:22][CH:23]=[CH2:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[C@@H:5]([O:21][CH2:22][CH2:23][CH3:24])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 58822773(S)-2-allyloxy-3-(4-benzyloxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 58822755(S)-3-(4-hydroxy-phenyl)-2-propoxy-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (S)-2-allyloxy-3-(4-benzyloxy-phenyl)-propionic acid ethyl ester (1.33 mmol, 450 mg) and 10% Pd/C (45 mg) in EtOH (15 mL) were stirred under hydrogen atmosphere (1 atm) for 18 hours. The mixture was filtered through celite and concentrated under vacuum to afford the title product. 1H-NMR (200.15 MHz, CDCl3): δ 7.10 (d, 4H, J=8.6), 6.73 (d, 2H, J=8.4), 5.90 (brs, 1H), 4.16 (q, 2H, J=7.3), 3.94 (t, 1H, J=6.7), 3.53–3.45 (m, 1H), 3.27–3.16 (m, 1H), 2.93 (d, 2H, J=6.5), 1.54 (m, 2H), 1.22 (t, 3H, J=7.3), 0.84 (t, 3H, J=7.5).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-16f974d918b1437b8bb142662cb3dfa1
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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