반응 #669936

반응 방정식

sodium cyclopentadienylide

1-bromo-2-fluoroethane

sodium hydroxide

hydrogen peroxide

2-methyl-2-butene

→

(RS)-3-(2-fluoroethyl)-3-cyclopenten-1-ol

수율 16.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도cooling and under nitrogen
2. 2
   기타The resulting reaction liquid
3. 3
   여과was filtered with cerite, and the filtrate
4. 4
   workup.ADDITIONwas added under ice-
5. 5
   온도cooling and under nitrogen stream to a tetrahydrofuran solution of disiamylborane
6. 6
   기타prepared
7. 7
   workup.STIRRINGthe resulting mixture was stirred for 8 hours
8. 8
   온도cooling to the reaction liquid
9. 9
   기타obtained above, and the resulting mixture
10. 10
    workup.STIRRINGwas stirred for 1 hour
11. 11
    기타The reaction liquid
12. 12
    기타thus obtained
13. 13
    추출was extracted two times with diethyl ether
14. 14
    세척The combined ether layer was washed with saturated aqueous sodium chloride solution
15. 15
    건조dried over anhydrous magnesium sulfate
16. 16
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
17. 17
    기타The residue obtained

실험 절차

To 25 ml of 2 M tetrahydrofuran solution of sodium cyclopentadienylide was added under ice-cooling and under nitrogen stream 6.3 g of 1-bromo-2-fluoroethane and stirred for 2 hours. The resulting reaction liquid was filtered with cerite, and the filtrate was added under ice-cooling and under nitrogen stream to a tetrahydrofuran solution of disiamylborane prepared by using 75 ml of 1 M borane-tetrahydrofuran complex and 18.5 ml of 2-methyl-2-butene and the resulting mixture was stirred for 8 hours. Then 3 N aqueous sodium hydroxide solution and 30% aqueous hydrogen peroxide were successively added under ice-cooling to the reaction liquid obtained above, and the resulting mixture was stirred for 1 hour. The reaction liquid thus obtained was extracted two times with diethyl ether. The combined ether layer was washed with saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was subjected to silica gel column chromatography to obtain 1.1 g of (RS)-3-(2-fluoroethyl)-3-cyclopenten-1-ol. Yield 16%

출처