反応 #1735

反応方程式

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

6-hydroxy-nicotinic acid

dicyclohexylcarbodiimide

→

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

収率 38.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   workup.WAITat 0° and the mixture was left
2. 2
   その他to react at room temperature overnight
3. 3
   ろ過The separated urea was filtered off
4. 4
   抽出the filtrate was extracted with ethyl acetate
5. 5
   洗浄washed twice with H2O
6. 6
   その他dried over Na2 SO4
7. 7
   その他the solvent was removed under reduced pressure

実験手順

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.).

出典