HCID 57431965, compound → HCID 57431964, compound

HRID 854527Notes

Reaction equation

HRID 854527 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][C:8]=1[CH2:21][CH2:22][CH3:23])[CH3:2].[H][H]>C1COCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH2:21][CH2:22][CH3:23])[CH3:2]

Participants

5

Reactant 2

HCID 57431965HCID 57431965, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57431964HCID 57431964, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-benzyloxy-2-propylphenoxy)acetic acid ethyl ester (0.60 g, 1.83 mmol) in THF (15 mL) is treated with 5% Pd/C (75 mg) and hydrogen (60 psi) at ambient temperature for 24 h. The mixture is filtered and concentrated. The crude product is purified by radial chromatography using 15% ethyl acetate in hexanes to give a tan solid (0.25 g, 57%). 1H NMR (400 MHz, CDCl3) δ 6.66 (d, J=2.9 Hz, 1H), 6.62 (d, J=8.8 Hz, 1H), 6.57 (dd, J=8.8, 2.9 Hz, 1H), 4.56 (s, 1H), 4.40 (s, 1H), 4.25 (q, J=7.2 Hz, 2H), 2.61 (t, J=7.6 Hz, 2H), 1.63 (q, J=7.5 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H); MS (FIA) m/e 239 (M+1).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated
  3. customThe crude product is purified by radial chromatography

Sources & evidence

ORD record
ord-3d5e4908f68d4df7a92f73a1a6b6cbd1
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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