Pyridine → (5-Trifluoromethanesulfonyloxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

HRID 426306Notes

Reaction equation

FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH2:16]([O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:22]=[C:23]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[CH:24]=[C:25](O)[CH:26]=1)[CH3:17].N1C=CC=CC=1>C(Cl)Cl>[CH2:16]([O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:22]=[C:23]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:30][CH:29]=2)[CH:24]=[C:25]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[CH:26]=1)[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoromethanesulphonic anhydride (570 mg, 2.0 mmol) was added drop wise to a solution of (5-hydroxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (546 mg, 1.69 mmol) and pyridine (0.41 mL, 5.0 mmol) in DCM (10 mL) at 0° C. The temperature was maintained at 0° C. for 15 mins before warming to room temperature and the mixture stirred for 18 hrs. The reaction was diluted with DCM, washed with H2O, Na2CO3, dil. HCl, brine, dried (MgSO4) and evaporated under reduced pressure to give a yellow oil. The residue was purified by flash column chromatography (EtOAc:petroleum ether), yield 695 mg (96%). 1H NMR (CDCl3) δ 7.72 (d, 2H), 7.66 (d, 2H), 7.54 (t, 1H), 7.39 (t, 1H), 7.28 (t, 1H), 4.19 (q, 2H), 3.73 (s, 2H), 1.28 (t, 3H).

Workup

temperaturebefore warming to room temperature
washwashed with H2O, Na2CO3, dil. HCl, brine
dry with materialdried (MgSO4)
customevaporated under reduced pressure
customto give a yellow oil
customThe residue was purified by flash column chromatography (EtOAc:petroleum ether), yield 695 mg (96%)

Sources & evidence

ORD record: ord-b88c34385d5a48ce831093e6188ca623
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106236B2

Reaction notes

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