Acetic Acid → 3-[4-({4'-[2-(Ethylsulfonyl)ethoxy]-2',6'-dimethylbiphenyl-3-yl}methoxy)-2-fluorophenyl]propanoic acid

HRID 273413Notes

Reaction equation

[CH2:1]([S:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[C:26]([F:37])[CH:25]=3)[CH:17]=2)=[C:11]([CH3:38])[CH:10]=1)(=[O:5])=[O:4])[CH3:2].C(O)(=O)C.O.S(=O)(=O)(O)O>C(OCC)(=O)C>[CH2:1]([S:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[C:26]([F:37])[CH:25]=3)[CH:17]=2)=[C:11]([CH3:38])[CH:10]=1)(=[O:4])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 3-[4-({4′-[2-(ethylsulfonyl)ethoxy]-2′,6′-dimethylbiphenyl-3-yl}methoxy)-2-fluorophenyl]propanoate (0.19 g, 0.35 mmol), acetic acid (4.5 mL), water (4.0 mL) and conc. sulfuric acid (0.65 mL) was stirred at 90° C. for 4 hrs. The reaction mixture was cooled, diluted with ethyl acetate, washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-ethyl acetate) to give the title compound (0.12 g, yield 61%) as colorless crystals.

Workup

temperatureThe reaction mixture was cooled
washwashed with water and saturated brine
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-ethyl acetate)

Sources & evidence

ORD record: ord-c600f68ac3164180ab62a61e89a05c46
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456218B2

Reaction notes

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