p-Aminoacetophenone → HCID 58230610, compound

HRID 451198Notes

Reaction equation

HRID 451198 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C:7]1[C:8]([CH:16]=O)=[CH:9][C:10]2[O:14][CH2:13][O:12][C:11]=2[CH:15]=1)([CH3:4])[CH3:3].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=1.[CH:28]1[CH2:32][CH:31]=[CH:30][CH:29]=1>C(#N)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3]>[CH3:4][Si:2]([C:5]#[C:6][C:7]1[C:8]([CH:16]2[CH:31]3[CH2:32][CH:28]=[CH:29][CH:30]3[C:20]3[CH:21]=[C:22]([C:25](=[O:27])[CH3:26])[CH:23]=[CH:24][C:19]=3[NH:18]2)=[CH:9][C:10]2[O:14][CH2:13][O:12][C:11]=2[CH:15]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 7468p-AminoacetophenoneHCID 7612CyclopentadieneHCID 10900934HCID 10900934, compound

Product 1

HCID 58230610HCID 58230610, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of the catalyst Sc(OTf)3 (0.032 g, 0.065 mmol, 10 mol %) in acetonitrile (0.2 mL) was added to the mixture of 6-trimethylsilanylethynyl-benzo[1,3]dioxole-5-carbaldehyde (0.160 g, 0.65 mmol), p-aminoacetophenone (0.0878 g, 0.65 mmol) and cyclopentadiene (0.214 g, 3.25 mmol) in acetonitrile (3 mL). The reaction was stirred at ambient temperature (˜23° C.) and the progress was monitored by thin layer chromatography. The reaction was complete after 2 hr. The reaction mixture was worked up by removal of solvent and other volatiles by evaporation under reduced pressure. The crude material was purified by preparative column chromatography using silica gel (SiO2) eluted with EtOAc/hexane (polar phase composition 8% EtOAc). The fractions containing pure product were evaporated in vacuo. The yield was 97%.

Workup

  1. customThe reaction mixture was worked up by removal of solvent and other volatiles by evaporation under reduced pressure
  2. customThe crude material was purified by preparative column chromatography
  3. washeluted with EtOAc/hexane (polar phase composition 8% EtOAc)
  4. additionThe fractions containing pure product
  5. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-c192d14d8984486c80ca5971cd9d68b6
Source dataset
uspto-grants-2013_07
Patent number
US08487100B2

Reaction notes

Loading…