2-Fluorophenoxy-3-(4-benzyloxyphenyl)-2-methyl-propionic acid ethyl ester → 2-(2-Fluorophenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester

HRID 1985128Notes

Reaction equation

HRID 1985128 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[F:29])([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:30])[C:5]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[F:29])([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 577190282-Fluorophenoxy-3-(4-benzyloxyphenyl)-2-methyl-propionic acid ethyl ester

Product 1

HCID 577192632-(2-Fluorophenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(4-Benzyloxy-phenyl)-2-(2-fluoro-phenoxy)-2-methyl-propionic acid ethyl ester (12.8 g, 31.34 mmol) is dissolved in ethanol (500 mL), treated with 10% palladium on carbon (6.0 g), and stirred under an atmosphere of hydrogen for 90 minutes. The suspension is filtered through celite and concentrated to provide 2-(2-Fluoro-phenoxy)-3-(4-hydroxy-phenyl)-2-methyl-propionic acid ethyl ester (9.65 g, 97%). The title compound is separated by chiral chromatography (Column OJ, 40% IPA in heptane, 1 mL/mmin, 240 nm UV. 1H NMR (400 MHz, CDCl3): δ 7.13 (d, 2H, J=8.0 Hz), 7.07-7.02 (m, 1H), 6.98-6.88 (m, 3H), 6.74 (d, 2H, J=8.0 Hz), 6.05 (s, 1H), 4.20 (q, 2H, J=6.9 Hz), 3.24, 3.16 (ABq, 2H, J=13.4 Hz), 1.39 (s, 3H), 1.23 (t, 3H, J=6.8 Hz).

Workup

  1. filtrationThe suspension is filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9f286c36ca4e46e386b9d8a9e7d9c5e6
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

Loading…