反応 #213917

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.ADDITIONis added 87 g
2. 2
   workup.STIRRINGthe mixture is stirred until an exotherm ensues
3. 3
   温度maintaining
4. 4
   その他the reaction exotherm at 65° C
5. 5
   workup.STIRRINGThe mixture is then stirred for 2.5 hours
6. 6
   workup.ADDITIONThe mixture is slowly poured into a stirred mixture of 100 ml
7. 7
   workup.STIRRINGThe mixture is stirred for 30 minutes
8. 8
   抽出The mixture is extracted with ether
9. 9
   洗浄The ether solution is washed with saturated sodium bicarbonate
10. 10
    乾燥dried over magnesium sulfate
11. 11
    その他The solvent is removed
12. 12
    workup.ADDITIONThe residue is mixed with petroleum ether
13. 13
    温度cooled in dry ice acetone
14. 14
    その他crystallization
15. 15
    その他The petroleum ether is decanted
16. 16
    その他the solid is dried at reduced pressure
17. 17
    その他to give 64.72 g

実験手順

To 191.4 g. of tris-trimethylsilyloxyethylene (Example 74) containing 15 drops of stannic tetrachloride under argon with stirring at 10° C. is added 87 g. of 5-bromopentanoyl chloride (Example 81) dropwise. After one-half of the acid chloride is 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 0.6N hydrochloric acid and 200 ml. of tetrahydrofuran. The mixture is stirred for 30 minutes and poured into brine. The 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 petroleum ether and cooled in dry ice acetone to induce crystallization. The petroleum ether is decanted and the solid is dried at reduced pressure to give 64.72 g. of the title compound.

出典