반응 #1735

반응 방정식

4-trimethylsilyl-(E)-but-2-en-1-ol

6-hydroxy-nicotinic acid

dicyclohexylcarbodiimide

→

4-trimethylsilanyl-(E)-but-2-enyl 6-hydroxy-nicotinate

수율 38.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.WAITat 0° and the mixture was left
2. 2
   기타to react at room temperature overnight
3. 3
   여과The separated urea was filtered off
4. 4
   추출the filtrate was extracted with ethyl acetate
5. 5
   세척washed twice with H2O
6. 6
   기타dried over Na2 SO4
7. 7
   기타the solvent was removed under reduced pressure

실험 절차

1.3 g of 4-trimethylsilyl-(E)-but-2-en-1-ol (synthesis described in J. Org. Chem. 1984, 49, 4092), 1.08 g of 6-hydroxy-nicotinic acid and 178 mg of 4-dimethylaminopyridine were placed in succession in 30 ml of abs. dimethylformamide. 1.77 g (1.1 eq.) of dicyclohexylcarbodiimide were added thereto at 0° and the mixture was left to react at room temperature overnight. The separated urea was filtered off, the filtrate was extracted with ethyl acetate, washed twice with H2O, dried over Na2 SO4 and the solvent was removed under reduced pressure. Flash chromatography on SiO2 (hexane/ethyl acetate=1/1) yielded 782 mg of 4-trimethylsilanyl-(E)-but-2-enyl 6-hydroxy-nicotinate as white crystals of m.p. 107°-110° (dec.).

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