p-Aminoacetophenone → HCID 4238068, compound

HRID 254803Notes

Reaction equation

HRID 254803 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)=[O:13].[CH:21]1[CH2:25][CH:24]=[CH:23][CH:22]=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]>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[CH:24]3[CH2:25][CH:21]=[CH:22][CH:23]3[C:16]3[CH:15]=[C:14]([C:12](=[O:13])[CH3:11])[CH:19]=[CH:18][C:17]=3[NH:20]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7468p-AminoacetophenoneHCID 7612CyclopentadieneHCID 312444-Methoxybenzaldehyde

Product 1

HCID 4238068HCID 4238068, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6342AcetonitrileSolvent2×

Procedure

4-Methoxybenzaldehyde (0.074 g, 0.5 mmol) and 4-aminoacetophenone (0.068 g 0.5 mmol) were heated to melting in a round bottom flask, then a solution of the catalyst Sc(OTf)3 (0.0248 g, 0.05 mmol, 10 mol %) in anhydrous acetonitrile (0.2 mL) was added to the molten solid, followed by a solution of cyclopentadiene (0.165 g, 2.5 mmol) in acetonitrile (3 mL). The reaction was stirred at rt for 2.30 h. The reaction mixture was concentrated under reduced pressure. The crude material was purified by preparative column chromatography using silica gel (SiO2) eluted with 10% EtOAc/Hexanes to give the product as a colorless solid (0.120 g, 76%).

Workup

  1. customto melting in a round bottom flask
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe crude material was purified by preparative column chromatography
  4. washeluted with 10% EtOAc/Hexanes

Sources & evidence

ORD record
ord-456a3f6f5fdb494db1e61d2f3e436e12
Source dataset
uspto-grants-2011_01
Patent number
US07875721B2

Reaction notes

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