Sustainable transesterification of β-ketoesters catalyzed by amine grafted on silica gel

Synlett

Volumn , Issue 12, 2004, Pages 2188-2190

  Hagiwara, Hisahiro ^a   Koseki, Aiko ^a   Isobe, Kohei ^a   Shimizu, Ken Ichi ^a   Hoshi, Takashi ^a   Suzuki, Toshio ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

ketoester; Amine catalyst; Silica gel support; Transesterification

Indexed keywords

ALCOHOL; AMINE; BETA KETO ESTER; ESTER; SILICA GEL; UNCLASSIFIED DRUG; XYLENE;

ACID BASE BALANCE; ANALYTIC METHOD; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; REACTION ANALYSIS; RECYCLING; SURFACE PROPERTY; TRANSESTERIFICATION;

EID: 5644253217     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831309     Document Type: Article

References (18)

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16. NDEAP was prepared according to the same procedure as ref.Sb, using N,N-diethyl-3-aminopropyl(trimethoxy)silane and silica gel. Nitrogen loading was 0.72 mmol/g according to combustion analysis.
17. Typical Experimental Procedure: To a stirred solution of menthol (2a, 156 mg, 1 mmol) and methyl acetoacetate (1a, 130 μL, 1.2 mmol) in anhyd xylene (4 mL) was added NDEAP pellets (279 mg, 0.72 mmol/g, 0.2 mmol) and the resulting mixture was heated at reflux for 7 h. After removal of the catalyst by filtration, the filtrate was evaporated to dryness to give a residue, which was purified by column chromatography on silica gel to give β-ketoester 3a (238 mg, 99%). The catalyst NDEAP was re-used intact for the subsequent reaction.
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