Reaktion #67988

Reaktionsgleichung

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

Lösungsmittel

tetrahydrofuran

ethyl acetate

Water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle