反应 #67988

反应方程式

sodium hydride

1-(1,3-thiazol-2-yl)ethanone

dimethyl carbonate

sodium hydride

hydrochloric acid

→

methyl 3-oxo-3-(1,3-thiazol-2-yl)propionate

溶剂

tetrahydrofuran

ethyl acetate

Water

反应条件

后处理

1. 1
   workup.ADDITIONwere added at 10° C
2. 2
   workup.STIRRINGthe mixture was stirred for 4 hours
3. 3
   其他The organic layer was separated
4. 4
   萃取the aqueous layer was extracted with ethyl acetate
5. 5
   洗涤the resultant solution was washed with an aqueous saturated sodium chloride solution
6. 6
   干燥dried over anhydrous magnesium sulfate
7. 7
   其他the solvent was removed under reduced pressure
8. 8
   其他The residue thus obtained
9. 9
   其他was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

实验过程

To 50 mL of a tetrahydrofuran solution containing 5.0 g of 1-(1,3-thiazol-2-yl)ethanone, 6.3 mL of dimethyl carbonate and 3.0 g of 60% sodium hydride were added at 10° C. The temperature of the reaction mixture was increased to room temperature, and the mixture was stirred for 16 hours. Thereto was further added 0.75 g of 60% sodium hydride, and the mixture was stirred for 4 hours. Water and ethyl acetate were then added thereto, and the reaction mixture was adjusted to pH 3.0 with 6 mol/L hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to obtain 2.3 g of a yellow oily substance, methyl 3-oxo-3-(1,3-thiazol-2-yl)propionate.

来源