Trifluoroacetic acid → HCID 11325941, compound

HRID 229144Notes

Reaction equation

HRID 229144 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:7][CH2:6][C:5](=[C:8]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]C(C)(C)C)=[O:18])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:31])[CH2:7][CH2:6][C:5](=[C:8]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68975577HCID 68975577, compound

Product 1

HCID 11325941HCID 11325941, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1,1-dimethylethyl (2E)-3-{4-[(4,4-dimethylcyclohexylidene)(4-hydroxyphenyl)methyl]phenyl}-2-propenoate (21) (0.24 g, 0.57 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (4 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 1 h and concentrated in vacuo to give an oil. The oil was dissolved in CH2Cl2 and the solvent was removed in vacuo to give a solid which was dried under vacuum at 90° C. to give 0.170 g (82%) of compound 22 as a pale tan solid. 1H NMR (400 MHz, DMSO-d6): δ 0.93 (s, 6H), 1.31 (m, 4H), 2.16 (m, 4H), 6.44 (d, J=15.9 Hz, 1H), 6.65 (d, J=8.4 Hz, 2H), 6.84 (d, J=8.3 Hz, 2H), 7.05 (d, J=7.9 Hz, 2H), 7.52 (d, J=15.9 Hz, 1H), 7.57 (d, J=8.1 Hz, 2H), 9.32 (s, 1H), 12.33 (br s, 1H). The compound was silated prior to EI analysis. HRMS (EI) Calcd for C30H42O3Si2: 506.2673 (M+.). Found: 506.2669.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give an oil
  3. customthe solvent was removed in vacuo
  4. customto give a solid which
  5. customwas dried under vacuum at 90° C.

Sources & evidence

ORD record
ord-4c266678aa2645ac897d904d3be40497
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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