An improved synthesis of methyl propiolate-1,2,3-13c3
β Scribed by Daniel F. Lieberman; Sun-Shine Yuan
- Publisher
- John Wiley and Sons
- Year
- 1982
- Tongue
- French
- Weight
- 190 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0022-2135
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β¦ Synopsis
Abstract
An high yield synthesis of the title compound from ^13^CO~2~ is described. A key to the success is direct formation of the ester from the intermediate lithium propiolateβ^13^C~3~.
π SIMILAR VOLUMES
Three selectively labeled propynes were prepared either with deuterium or carbon-13 at position 3 and doubly labeled with carbon-13 at positions 1 and 2 by an alkylation reaction from the corresponding labeled or unlabeled monolithio acetylides and dimethylsulfates. Their lithiation with nBuLi gave
The title compound is obtained from sodium acetate-1 -C by a shorter synthesis than the usual one . In the last step, acetyl chloride-1 J3C is reduced by tri- 13 butyltin hydride with palladium(0) complexe . ## Kev word. Ethanal, Carbon labelling Ethanal has a widespread use in synthesis of label
2-Ethoxy-1-methyl-5-pymlidinone (1) was reacted with ethyl [3,4-'3C2]acetoacetate (2) in the presence of T i c 4 to give ethyl [3,4-13C2]-2-( 1'-methyl-5'oxo-2'-pyrrolidinyl)-3-oxobutanoate (3) in 85% yield. Decarboethoxylation of ethyl [3,4-13C2]-2-( l'-methyl-5'-oxo-2'-pyrrolidiny1)-3-oxobutanoate