메뉴 건너뛰기




Volumn 48, Issue 37, 2007, Pages 6531-6534

A simple one-pot synthesis of 3-alkoxy-3-cyanocarboxylic acids: a rapid entry to new GABA derivatives

Author keywords

3 Alkoxy 3 cyanocarboxylic acids; 3 Alkoxy carboxylic acids; 3 Cyanocarboxylic acids; Carboxylic acids

Indexed keywords

4 AMINOBUTYRIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; SODIUM CYANIDE;

EID: 34547766630     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.060     Document Type: Article
Times cited : (13)

References (42)
  • 34
    • 34547742763 scopus 로고    scopus 로고
    • note
    • General procedure for the synthesis of 3-alkoxy-3-cyano carboxylic acids 2: To a solution of the enones 1 (5.0 mmol) in THF (3.0 mL) a solution of sodium cyanide (0.24 g, 5.0 mmol) in water (3.0 mL) was added, under stirring, at room temperature. The reaction mixture was stirred for 30 min and a new addition of a solution of sodium cyanide (0.24 g, 5.0 mmol) in water (3 mL) was added and the stirring was continued for 1-6 h, at room temperature. The products 2a-h were isolated through two extractions; in the first, the pH is basic from the reaction (pH ∼10) and the solution was extracted with ethyl ether (2 × 20 mL) to eliminate possible unreacted starting material. In the second extraction, the pH was lowered to about three with the addition of 1 M solution of hydrochloric acid and the solution was extracted with ethyl ether (2 × 20 mL) to recover the products 2a-h in the organic phase. The organic phase was dried under magnesium sulfate, filtered, and the solvent was evaporated to render 3-alkoxy-3-cyanocarboxylic acids 2a-h, as oils, in good yields, and high purity.
  • 37
    • 34547766077 scopus 로고    scopus 로고
    • note
    • 2),...


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.