反応 #214273

反応方程式

hydrochloric acid

tetrahydrofuran

5-bromopentanoyl chloride

5-bromopentanoylchloride

→

title compound

6-bromo-1-hydroxy-2-hexanone

溶媒

brine

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture is stirred until an exotherm ensues
2. 2
   温度maintaining
3. 3
   その他the reaction exotherm at 65° C
4. 4
   workup.STIRRINGThe mixture is then stirred for 2.5 hours
5. 5
   workup.STIRRINGThe mixture is stirred for 30 minutes
6. 6
   抽出Th mixture is extracted with ether
7. 7
   洗浄The ether solution is washed with saturated sodium bicarbonate
8. 8
   乾燥dried over magnesium sulfate
9. 9
   その他The solvent is removed
10. 10
    workup.ADDITIONThe residue is mixed with petrolium ether
11. 11
    温度cooled in dry-ice-acetone
12. 12
    その他crystallization
13. 13
    その他The petrolium ether is decanted
14. 14
    その他the solid is dried at reduced pressure

実験手順

To 191.4 g of tris-trimethylsilyloxyethylene (Example 267) containing 15 drops of stannic tetrachloride under argon with stirring at 10° C. is added 87 g of 5-bromopentanoyl chloride (Example 274) dropwise. After one-half of the acid chloride added, the mixture is stirred until an exotherm ensues. The remaining acid chloride is added dropwise maintaining the reaction exotherm at 65° C. The mixture is then stirred for 2.5 hours. The mixture is slowly poured into a stirred mixture of 100 ml of 0.6 N hydrochloric acid and 200 ml of tetrahydrofuran. The mixture is stirred for 30 minutes and poured into brine. Th mixture is extracted with ether. The ether solution is washed with saturated sodium bicarbonate and dried over magnesium sulfate. The solvent is removed. The residue is mixed with petrolium ether and cooled in dry-ice-acetone to induce crystallization. The petrolium ether is decanted and the solid is dried at reduced pressure to give 64.72 g of the title compound.

出典