Trifluoroacetic acid → HCID 89647559, compound

HRID 2281003Notes

Reaction equation

HRID 2281003 reaction equation
[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][C:18]([F:32])([F:31])[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](/[CH:26]=[CH:27]/[N+:28]([O-:30])=[O:29])[CH:21]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:9][C@@H:27]([N+:28]([O-:30])=[O:29])[C@H:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][C:18]([F:17])([F:31])[F:32])[CH:21]=2)[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 247211421-[(1E)-2-Nitroethenyl]-3-(trifluoromethoxy)benzene

Product 1

HCID 89647559HCID 89647559, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine was added to a solution of 1-trifluoromethoxy-3-((E)-2-nitro-vinyl)-benzene (6.00 g; 35.90 mmol) in DCM (50 ml). The reaction solution was cooled to 0° C., TFA (0.30 ml; 3.95 mmol) was added dropwise, and stirred overnight at RT. The reaction solution was washed with H2O and brine, dried over MgSO4, filtered, and concentrated. The crude material was purified via Biotage (340 g column) eluting with 5% EtOAc in hexane to provide the desired product 5.5 g, yield 51%.

Workup

  1. washThe reaction solution was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified via Biotage (340 g column)
  6. washeluting with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-49e97463dcff49ef8509b944b50e40d8
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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