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

HRID 229200Notes

Reaction equation

HRID 229200 reaction equation
FC(F)(F)C(O)=O.[C:8]1(=[C:14]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25]C(C)(C)C)=[O:24])=[C:17]([F:30])[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C(Cl)Cl>[C:8]1(=[C:14]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[C:17]([F:30])[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86613509tert-Butyl (2E)-3-{4-[cyclohexylidene(4-hydroxyphenyl)methyl]-2-fluorophenyl}prop-2-enoate

Product 1

HCID 11337112(2E)-3-{4-[Cyclohexylidene(4-hydroxyphenyl)methyl]-2-fluorophenyl}-2-propenoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.5 mL) was added dropwise to 90 (180 mg, 0.551 mmol) dissolved in CH2Cl2 (3 mL) at 0° C. The reaction mixture was stirred at RT for 2 h and the volatiles were removed under reduced pressure. Water (30 mL) was added and the mixture was extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (30 mL), brine (30), and dried over MgSO4. Concentration followed by recrystallization (EtOAc) afforded 99 mg (64%) of 91 as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 1.52 (br s, 6H), 2.13 (br s, 4H), 6.51 (d, J=16.0 Hz, 1H), 6.67 (d, J=8.4 Hz, 2H), 6.85-6.91 (m, 4H), 7.59 (d, J=16.0 Hz, 1H), 7.72 (t, J=8.1 Hz, 1H), 9.36 (s, 1H), 12.51 (br s, 1H). LRMS (APCI): m/z 353 (M+H)+.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. additionWater (30 mL) was added
  3. extractionthe mixture was extracted with EtOAc (3×20 mL)
  4. washThe combined organic layers were washed with water (30 mL), brine (30)
  5. dry with materialdried over MgSO4
  6. concentrationConcentration
  7. customfollowed by recrystallization (EtOAc)

Sources & evidence

ORD record
ord-3895b92a704943978b5d426d2186d653
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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