Trifluoroacetic acid → HCID 11066560, compound

HRID 577752Notes

Reaction equation

HRID 577752 reaction equation
[F:1][C:2]([F:11])([F:10])/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)(C(F)(F)F)=O.[CH2:19]([N:26]([CH2:30][Si](C)(C)C)[CH2:27]OC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:19]([N:26]1[CH2:30][C@@H:3]([C:2]([F:10])([F:11])[F:1])[C@H:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

Product 1

HCID 11066560HCID 11066560, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-ethyl 4,4,4-trifluorobut-2-enoate (100 g, 0.6 mol) in DCM (1.8 L) was added dropwise TFA (20.52 g, 0.18 mol) at 0° C. and then N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methanamine (170.64 g, 0.72 mol) was added and the resulting mixture was stirred at rt overnight. The reaction mixture was washed with sat. aqueous NaHCO3 (two×500 mL), dried over Na2SO4 and concentrated in vacuo and the residue was purified by silica column chromatography eluted with petroleum ether/EtOAc=100:1 to give the title compound (142 g, 79% yield) as a yellow oil.

Workup

  1. washThe reaction mixture was washed with sat. aqueous NaHCO3 (two×500 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by silica column chromatography
  5. washeluted with petroleum ether/EtOAc=100:1

Sources & evidence

ORD record
ord-f54ab73d6c2a43d09c3c930358b4c4e2
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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