Reaction #1735

Reaction equation

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

6-hydroxy-nicotinic acid

dicyclohexylcarbodiimide

→

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

Yield 38.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   workup.WAITat 0° and the mixture was left
2. 2
   Otherto react at room temperature overnight
3. 3
   FiltrationThe separated urea was filtered off
4. 4
   Extractionthe filtrate was extracted with ethyl acetate
5. 5
   Washwashed twice with H2O
6. 6
   Otherdried over Na2 SO4
7. 7
   Otherthe solvent was removed under reduced pressure

Procedure

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.).

Source