Trifluoroacetic acid → (2E)-3-{4-[bicyclo[3.3.1]non-9-ylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoic acid

HRID 2100055Notes

Reaction equation

HRID 2100055 reaction equation
[CH:1]12[C:9](=[C:10]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[C:11]3[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([O:21]C(C)(C)C)=[O:20])=[CH:13][CH:12]=3)[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.C(O)(C(F)(F)F)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[CH:5]12[C:9](=[C:10]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[C:11]3[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=3)[CH:1]([CH2:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689795521,1-Dimethylethyl (2E)-3-{4-[bicyclo[3.3.1]non-9-ylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoate

Product 1

HCID 11211051(2E)-3-{4-[bicyclo[3.3.1]non-9-ylidene(4-hydroxyphenyl)methyl]phenyl}-2-propenoic acidYield 74.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 44 (0.32 g, 0.755 mmol) in CH2Cl2 (4 mL) was added TFA (4 mL) slowly. The stirred reaction mixture was allowed to warm to RT over a period of 3 h. The reaction mixture was concentrated to give a yellow solid. The solid was dissolved in toluene, and the solution was concentrated to give a powder. The powder was triturated with CH2Cl2 and dried to give compound 45 as a tan powder (0.21 g, 74%). 1H NMR (400 MHz, DMSO-d6): δ 1.50-1.53 (m, 2H), 1.72 (s, 8H), 1.93-2.01 (m, 2H), 2.53-2.60 (m, 2), 6.43 (d, J=16.1 Hz, 1H), 6.66 (d, J=8.4 Hz, 2H), 6.88 (d, J=8.3 Hz, 2H), 7.09 (d, J=7.8 Hz, 2H), 7.52 (d, J=16.0 Hz, 1H), 7.57 (d, J=8.1 Hz, 2H), 9.30 (s, 1H), 12.33 (s, 1H). The compound was silated prior to EI analysis. HRMS (EI) Calcd for C31H42O3Si2: 518.2673 (M+). Found: 518.2685.

Workup

  1. customThe stirred reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. customto give a yellow solid
  4. concentrationthe solution was concentrated
  5. customto give a powder
  6. customThe powder was triturated with CH2Cl2
  7. customdried

Sources & evidence

ORD record
ord-b1c4f51618c2419a98989b607433f0d7
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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