Trifluoroacetic acid → HCID 10280152, compound

HRID 1836308Notes

Reaction equation

HRID 1836308 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:11]([O:13][CH2:14][CH3:15])=[CH2:12].FC(F)(F)C(O)=O.[O:23]([CH2:41][C:42]([CH3:46])([CH3:45])[CH:43]=O)[Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[O:23]([CH2:41][C:42]([CH:46]1[CH2:12][CH:11]([O:13][CH2:14][CH3:15])[C:9]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=2)[NH:8]1)([CH3:45])[CH3:43])[Si:24]([C:37]([CH3:38])([CH3:39])[CH3:40])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 74754-NitroanilineHCID 8023Ethyl vinyl etherHCID 10936741HCID 10936741, compound

Product 1

HCID 10280152HCID 10280152, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Nitroaniline (200 mg), 0.15 ml of ethyl vinyl ether, and 0.1 ml of trifluoroacetic acid were dissolved in 5 ml of acetonitrile, and 500 mg of 3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropionaldehyde was added at 0° C. After 6 hours of stirring at room temperature, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=10:1-8:1) to obtain 34 mg of the title compound. Its physical properties are shown below.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=10:1-8:1)

Sources & evidence

ORD record
ord-c1bf40156aff4f27a1221341f4fb4c8e
Source dataset
uspto-grants-2004_08
Patent number
US06777427B2

Reaction notes

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