An efficient method for α-alkylation of γ-butyrolactone

Chinese Chemical Letters

Volumn 13, Issue 11, 2002, Pages 1039-1042

  Meng, Yuan Ru ^a   Guan, Ye Di ^a  

^a NONE

Author keywords

Alkylation of butyrolactone; Catalytic transfer hydrogenation; Condensation; Pd C sodium hypophosphite

Indexed keywords

ALDEHYDE; ALKENYL GROUP; CARBON; GAMMA BUTYROLACTONE; PALLADIUM;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; HYDROGENATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS;

EID: 19944381524     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (5)

1. a) J. L. Hermann and R. H. Schlessinger, J.C.S. Chem. Comm., 1973, 711.
2. b) Gary H. Posner and Gary L. Loomis, J.C.S. Chem. Comm., 1972, 892.
3. Xue Wang, Yedi Guan, Chin. Chem. Lett., 1993, 4, 407.
4. General procedure of preparation of 1a∼f, 2a∼b, 3a: the solution of aromatic aldehyde (5 mmol), γ-butyrolactone (5 mmol) in anhydrous methyl alcohol was added dropwise to methyl alcohol solution of NaOEt (10 mmol) in ice-cooling. The mixture was stirred at 0-10°C for 3 hours. Then, the product was precipitate.
5. General procedure of the catalytic transfer hydrogenation: the α-alkenyl-γ-butyrolactone (3∼5 mmol) was dissolved in ethanol, heating to refluxing, then Pd/C (10%) was added (10%w/w starting compound). Then the solution of sodium hypophosphite in water was added dropwise. The mixture was stirred at room temperature for 3-5 h. Then the catalyst was filtered off and the mixture was extracted with ethyl acetate after removing ethanol. The product was gained from the organic phase after removing solvent or by conventional column chromatography if necessary.