Sustainable self-aldol condensation of unmodified aldehyde: A combination of ionic liquid and heterogeneous secondary-amine grafted on silica

Synlett

Volumn , Issue 6, 2003, Pages 873-875

  Hamaya, Jun ^a   Suzuki, Toshio ^a   Hoshi, Takashi ^a   Shimizu, Ken Ichi ^a   Kitayama, Yoshie ^a   Hagiwara, Hisahiro ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

Aldehydes; Aldol reactions; Amine; Catalyst; Ionic liquid; Silica support

Indexed keywords

ALDEHYDE DERIVATIVE; AMINE; PROPYLAMINE; SILICON DIOXIDE;

ALDOL REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; POLYMERIZATION;

EID: 0037617914     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

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26. 2 was added a solution of N-metlyl-3-aminopropyl(triethoxy)silane (2.54 g, 10.8 mmol) in toluene (15 mL). The resulting mixture was heated at reflux for 12 h. The solid was filtered off, washed with toluene and acetone and dried at 100°C for 6 h. Nitrogen loading was 0.75 mmol/g according to combustion analysis.
27. 2O layer was evaporated in vacuo and the residue was purified by medium-pressure LC (eluent: EtOAc:n-hexane = 1:5) to give enal 2 (122 mg, 83%). The ionic liquid involving silica pellets was heated at 70°C for 1 h at 1.5 mmHg and used for subsequent reaction.