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

HRID 1716031Notes

Reaction equation

HRID 1716031 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]([CH3:30])[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]([CH3:30])[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689758311,1-Dimethylethyl(2E)-3-{4-[cyclohexylidene(4-hydroxyphenyl)methyl]-2-methylphenyl}-2-propenoate

Product 1

HCID 11360031(2E)-3-{4-[Cyclohexylidene(4-hydroxyphenyl)methyl]-2-methylphenyl}-2-propenoic acidYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.0 mL) was added dropwise to 68 (210 mg, 0.519 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 chromatographed on silica gel (20:1 CH2Cl2:MeOH) and recrystallized (EtOAc:hexanes) to afford 138 mg (76%) of 69 as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ1.51 (br s, 6H), 2.13 (m, 4H), 2.30 (s, 3H), 6.35 (d, J=16.0 Hz, 1H), 6.66 (d, J=8.2 Hz, 2H), 6.82-6.91 (m, 4H), 7.59 (d, J=7.9 Hz, 1H), 7.75 (d, J=16.0 Hz, 1H), 9.31 (s, 1H), 12.36 (br s, 1H). LRMS (ESI): m/z 349 (M+H)+.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customThe residue was chromatographed on silica gel (20:1 CH2Cl2:MeOH)
  3. customrecrystallized (EtOAc:hexanes)

Sources & evidence

ORD record
ord-4847a6c6be9a4a8397b1b32ee76c3c81
Source dataset
uspto-grants-2010_09
Patent number
US07799828B2

Reaction notes

Loading…