Self-aldol condensation of unmodified aldehydes catalysed by secondary-amine immobilised in FSM-16 silica

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9073-9075

  Shimizu, Ken Ichi ^a   Hayashi, Eidai ^a   Inokuchi, Takuro ^a   Kodama, Tatsuya ^a   Hagiwara, Hisahiro ^a   Kitayama, Yoshie ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

Aldehydes; Aldol reactions; Amine catalyst; Mesoporous silica

Indexed keywords

ALDEHYDE DERIVATIVE; AMINE; SILICON DIOXIDE;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES;

EID: 0037049167     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02313-4     Document Type: Article

References (23)

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19. Typically, 2.0 g of the FSM-16 sample was evacuated at 150°C and then toluene (20 mL) containing N-methyl-3-aminopropyl(triethoxy)silane (2 mmol) was introduced. The mixture was heated at reflux temperature for 3 h and the solid was filtered off, washed with toluene and acetone and dried at 100°C overnight.
20. Before the reaction, the catalyst was dried in air at 150°C for 1 h. The reaction was carried out by stirring the reaction mixture containing aldehyde (1 mmol) in dry toluene (5 mL) at reflux temperature under nitrogen atmosphere. Progress of the reaction was monitored by GC analyses of aliquots using o-xylene as an internal standard.
21. The geometry of the products from n-hexanal, n-decanal and hydrocinnamaldehyde was determined to be E from NOE enhancements between aldehydic and olefinic protons.
22. The yield was lower than the conversion of n-hexanal. This may be due to the oligomerisation or the adsorption of aldehydes on the catalyst.
23. 3 solution.