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

HRID 229185Notes

Reaction equation

HRID 229185 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11](/[CH:29]=[CH:30]/[C:31]([O:33]C(C)(C)C)=[O:32])[CH:12]=[CH:13][C:14]=1[C:15](=[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11](/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32])[CH:12]=[CH:13][C:14]=1[C:15](=[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689772451,1-Dimethylethyl (2E)-3-{3-chloro-4-[cyclohexylidene(4-hydroxyphenyl)-methyl]phenyl}-2-propenoate

Product 1

HCID 11337637(2E)-3-{3-Chloro-4-[cyclohexylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.0 mL) was added dropwise to 73 (300 mg, 0.706 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 silca gel (20:1 CH2Cl2:MeOH) to afford 225 mg (86%) of 74 as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 1.53 (br s, 6H), 1.88 (br s, 2H), 2.20 (m, 2H), 6.54 (d, J=16.0 Hz, 1H), 6.65 (d, J=8.8 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 7.23 (d, J=7.9 Hz, 1H), 7.52 (d, J=16.0 Hz, 1H), 7.59 (d, J=7.9 Hz, 1H). LRMS (ESI): m/z 370 (M+H)+.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customThe residue was chromatographed on silca gel (20:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-b114bbe5009d4351b282c6ba0e91d39c
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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