HCID 58801820, compound → HCID 58801823, compound

HRID 1985149Notes

Reaction equation

HRID 1985149 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]([OH:22])([CH3:21])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[C:5]([OH:22])([CH3:21])[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 58801820HCID 58801820, compound

Product 1

HCID 58801823HCID 58801823, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(4-Benzyloxy-phenyl)-2-hydroxy-2-methyl-propionic acid ethyl ester (5.9 g, 18.77 mmol) is dissolved in ethanol (375 mL), treated with 10% palladium on carbon (2.95 g), and stirred under an atmosphere of hydrogen for 2 h. The suspension is filtered and concentrated to provide the title compound. 1H NMR (400 MHz, CDCl3): δ 7.00 (d, 2H, J=8.3 Hz), 6.69 (d, 2H, J=8.3 Hz), 4.18-4.13 (m, 2H), 2.99, 2.83 (ABq, 2H, J=13.7 Hz), 1.47 (s, 3H), 1.24 (t, 3H, J=7.34 Hz). Rf=0.58 in 50% acetone in hexanes.

Workup

  1. filtrationThe suspension is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2b04b17e19814e69b3f8983fae49348a
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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