反应详情

温度

30 °C

Trimethyl borate (15 mL), zinc powder (washed in advance with dilute hydrochloric acid and dried for use, 4.24 g), and tert-butyl bromoacetate (9.91 mL, 48.6 mmol) were added in this order to a tetrahydrofuran solution (15 mL) of hex-5-en-2-one (5.29 g, 53.9 mmol), and the mixture was heated to 30° C. for 30 minutes using an oil bath, then brought to room temperature, and stirred for 3 hours. The mixture was separated into organic and aqueous layers by the addition of glycerol, a saturated aqueous solution of ammonium chloride, and saturated saline, and the aqueous layer was then subjected to extraction with diethyl ether. These organic layers were combined, then washed with saturated saline, and then dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. To the residue, a 2 N potassium hydroxide-methanol solution (50 mL) was added, and the mixture was stirred at room temperature for 6 hours. The solvent was distilled off under reduced pressure. To the residue, a 1 N aqueous sodium hydroxide solution was then added, followed by washing with diethyl ether. The aqueous layer was made acidic using concentrated hydrochloric acid under ice cooling, followed by extraction with diethyl ether. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the compound of interest as a pale yellow oil substance (5.24 g, 75%).

1. custombrought to room temperature
2. customThe mixture was separated into organic and aqueous layers
3. additionby the addition of glycerol
4. extractiona saturated aqueous solution of ammonium chloride, and saturated saline, and the aqueous layer was then subjected to extraction with diethyl ether
5. washwashed with saturated saline
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationthe solvent was then distilled off under reduced pressure
8. additionTo the residue, a 2 N potassium hydroxide-methanol solution (50 mL) was added
9. stirringthe mixture was stirred at room temperature for 6 hours
10. distillationThe solvent was distilled off under reduced pressure
11. additionTo the residue, a 1 N aqueous sodium hydroxide solution was then added
12. washby washing with diethyl ether
13. extractionfollowed by extraction with diethyl ether
14. washThe organic layer was washed with saturated saline
15. dry with materialdried over anhydrous magnesium sulfate
16. distillationThe solvent was distilled off under reduced pressure
17. customto obtain the compound of interest as a pale yellow oil substance (5.24 g, 75%)