Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionate → HCID 20823128, compound

HRID 585288Notes

Reaction equation

HRID 585288 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=1)([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(OC(=O)C(C)(OC1C=CC=CC=1)CC1C=CC(O)=CC=1)C>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:30])[C:5]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Br:29])[CH:24]=1)([CH3:21])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 11220314Ethyl 3-(4-hydroxyphenyl)-2-methyl-2-phenoxypropionateHCID 20823145HCID 20823145, compound

Product 1

HCID 20823128HCID 20823128, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(4-Benzyloxy-phenyl)-2-(3-bromo-phenoxy)-2-methyl-propionic acid ethyl ester (3.7 g, 7.8 mmol) was dissolved in ethanol (140 mL), treated with 5% palladium on carbon (0.37 g), and stirred under an atmosphere of hydrogen for 2 h. The suspension was filtered through celite and concentrated in vacuo. The residue was purified by flash column chromatography (25% ethyl acetate in hexanes) to provide a mixture of the title compound and 3-(4-Hydroxyphenyl)-2-methyl-2-phenoxy-propionic acid ethyl ester as a light yellow oil (2.8 g, 94%). 1H NMR (400 MHz, CDCl3): δ 7.24-6.94 (m, 4H), 6.83-6.80 (m, 1H), 6.75-6.71 (m, 3H), 5.12 (s, 1H), 4.19 (q, 2H, J=7.04 Hz), 3.24 (d, 1H, J=13.69 Hz), 3.06 (d, 1H, J=13.69 Hz), 1.40 (s, 3H), 1.26-1.17 (m, 3H). MS [EI−] 377 (M−H)+. Rf=0.24 in 25% ethyl acetate in hexanes.

Workup

  1. filtrationThe suspension was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography (25% ethyl acetate in hexanes)
  4. customto provide

Sources & evidence

ORD record
ord-50720edbe1f34c8d93511b9feef1d644
Source dataset
uspto-grants-2005_08
Patent number
US06930120B2

Reaction notes

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