تفاعل #1735

معادلة التفاعل

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

6-hydroxy-nicotinic acid

dicyclohexylcarbodiimide

→

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

المردود 38.0%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.WAITat 0° and the mixture was left
2. 2
   أخرىto react at room temperature overnight
3. 3
   ترشيحThe separated urea was filtered off
4. 4
   استخلاصthe filtrate was extracted with ethyl acetate
5. 5
   غسيلwashed twice with H2O
6. 6
   أخرىdried over Na2 SO4
7. 7
   أخرىthe solvent was removed under reduced pressure

الإجراء التجريبي

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.).

المصدر