Trifluoroacetic acid → HCID 11961296, compound

HRID 2241022Notes

Reaction equation

HRID 2241022 reaction equation
[C:1]1(=[C:8]([C:24]2[CH:29]=[CH:28][CH:27]=[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)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1(=[C:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:9]2[CH:10]=[CH:11][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:13][CH:14]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86621470HCID 86621470, compound

Product 1

HCID 11961296HCID 11961296, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 2 (0.77 g, 2.24 mmol) in CH2Cl2 (25 mL) at 0° C., was added, drop wise, TFA over 15 min. The pale yellow, reaction was stirred at 0° C. for 1 h then allowed to stand at RT for 15 min. The reaction was concentrated to a viscous oil, redissolved in CH2Cl2 (20 mL) and reconcentrated to a gummy solid. The crude product was crystallized from ether/hexanes to afford the title compound (3) as a white solid (0.30 g, 41%). 1H NMR (300 MHz, DMSO-d6): δ 1.59 (s, 8H), 2.29 (br s, 4H), 6.52 (d, J=16 Hz, 1H), 7.15-7.39 (m, 7H), 7.59 (d, J=16 Hz, 1H), 7.66 (d, J=8.3 Hz, 2H), 12.41 (s, 1H). LRMS (APCI): m/z 433 (M+H)+. Anal. Calcd for C23H24O2: C, 83.07; H, 7.30. Found: C, 82.73; H, 7.25.

Workup

  1. customThe pale yellow, reaction
  2. waitto stand at RT for 15 min
  3. concentrationThe reaction was concentrated to a viscous oil
  4. dissolutionredissolved in CH2Cl2 (20 mL)
  5. customThe crude product was crystallized from ether/hexanes

Sources & evidence

ORD record
ord-26468da23d7a44d88991ed6e7f2f5d80
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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