反应详情

In dichloromethane (20 ml), methyl 4-hydroxymethylbenzoate (1.00 g) was dissolved, followed by the addition of triethylamine (0.9 ml). Under ice cooling, a solution of methanesulfonyl chloride (0.70 g) in dichloromethane (dichloromethane: 5 ml) was added to the resulting solution. The resulting mixture was stirred at room temperature for 15 hours. After dilution with dichloromethane, the reaction mixture was washed with water and was then dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was dissolved in acetonitrile (12 ml). To the resulting solution, potassium cyanide (0.80 g) and 18-Crown-6 (0.16 g) were added, followed by stirring at room temperature for 40 hours. After concentration under reduced pressure, the concentrate was diluted with dichloromethane, washed with water and then, dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (dichloromethane), whereby colorless crystals (0.91 g, 86%) was obtained. A portion of the resulting crystals was recrystallized from a mixed solvent of hexane and ethyl acetate, whereby colorless crystals were obtained.

1. washAfter dilution with dichloromethane, the reaction mixture was washed with water
2. dry with materialwas then dried over anhydrous sodium sulfate
3. customThe residue obtained
4. distillationby distilling off the solvent under reduced pressure
5. dissolutionwas dissolved in acetonitrile (12 ml)
6. additionTo the resulting solution, potassium cyanide (0.80 g) and 18-Crown-6 (0.16 g) were added
7. stirringby stirring at room temperature for 40 hours
8. concentrationAfter concentration under reduced pressure
9. additionthe concentrate was diluted with dichloromethane
10. washwashed with water
11. dry with materialdried over anhydrous sodium sulfate
12. customThe residue obtained
13. distillationby distilling off the solvent under reduced pressure
14. customwas purified by chromatography on a silica gel column (dichloromethane)