Trifluoroacetic acid → (2E)-3-{4-[Cyclohexylidene(3-fluoro-4-hydroxyphenyl)methyl]phenyl}-2-propenoic acid

HRID 229195Notes

Reaction equation

HRID 229195 reaction equation
FC(F)(F)C(O)=O.[C:8]1(=[C:14]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([F:37])[CH:31]=2)[C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25]C(C)(C)C)=[O:24])=[CH:17][CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C(Cl)Cl>[C:8]1(=[C:14]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([F:37])[CH:31]=2)[C:15]2[CH:16]=[CH:17][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:19][CH:20]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689762991,1-Dimethylethyl (2E)-3-{4-[cyclohexylidene(3-fluoro-4-hydroxyphenyl)-methyl]phenyl}-2-propenoate

Product 1

HCID 11302608(2E)-3-{4-[Cyclohexylidene(3-fluoro-4-hydroxyphenyl)methyl]phenyl}-2-propenoic acidYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.0 mL) was added dropwise to 84 (179 mg, 0.438 mmol) dissolved in CH2Cl2 (2 mL) at 0 (C. The reaction mixture was stirred at RT for 3 h and the volatiles were removed under reduced pressure. The residue was recrystallized (EtOAc:hexanes) to afford 120 mg (78%) of 85 as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 1.52 (br s, 6H), 2.13 (m, 4H), 6.45 (d, J=16.0 Hz, 1H), 6.67 (d, J=8.2 Hz, 1H), 6.76 (dd, J=12.3 Hz, 1.7 Hz, 1H), 6.85 (t, J=8.8 Hz, 1H), 7.08 (d, J=8.1 Hz, 2H), 7.53 (d, J=16.0 Hz, 1H), 7.58 (d, J=8.1 Hz, 2H) 9.76 (s, 1H), 12.31 (br s, 1H). LRMS (ESI): m/z 353 (M+H)+.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customThe residue was recrystallized (EtOAc:hexanes)

Sources & evidence

ORD record
ord-3c862d8ec8ad4f129e05d32369ea1d1a
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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