Trifluoroacetic acid → HCID 15917268, compound

HRID 642850Notes

Reaction equation

HRID 642850 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:19])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:12][C:11]([F:13])([F:14])[C:10]([C:7]1[CH:8]=[CH:9][C:4]([CH:3]=[O:2])=[CH:5][CH:6]=1)([OH:19])[C:15]([F:16])([F:18])[F:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58592739HCID 58592739, compound

Product 1

HCID 15917268HCID 15917268, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Dimethoxymethyl-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (350 mg, 1.1 mmol) was dissolved in DCM (5 ml). A 50% aqueous TFA (5 ml) was added and the solution was allowed to stir for 2h. The solvent was removed under vacuum, and the reaction mixture was partitioned between ethyl acetate and a 1M sodium carbonate solution. The organic layer was washed with carbonate two additional times, and then it was washed with brine. It was dried over MgSO4, and the solvent was removed to yield the title product (300 mg (100%), 1.1 mmol) as a white solid. 1H NMR (DMSO-d6) δ=10.1 (s, 1H), 9.05 (s, 1H), 8.12 (d, J=8.5 Hz, 2H), 7.96 (d, J=8.2 Hz, 2H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with carbonate two additional times
  4. washit was washed with brine
  5. dry with materialIt was dried over MgSO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-1338555a4cc04ecdb85f1bd348d699cd
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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