反応 #669936

反応方程式

sodium cyclopentadienylide

1-bromo-2-fluoroethane

sodium hydroxide

hydrogen peroxide

2-methyl-2-butene

→

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

収率 16.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度cooling and under nitrogen
2. 2
   その他The resulting reaction liquid
3. 3
   ろ過was filtered with cerite, and the filtrate
4. 4
   workup.ADDITIONwas added under ice-
5. 5
   温度cooling and under nitrogen stream to a tetrahydrofuran solution of disiamylborane
6. 6
   その他prepared
7. 7
   workup.STIRRINGthe resulting mixture was stirred for 8 hours
8. 8
   温度cooling to the reaction liquid
9. 9
   その他obtained above, and the resulting mixture
10. 10
    workup.STIRRINGwas stirred for 1 hour
11. 11
    その他The reaction liquid
12. 12
    その他thus obtained
13. 13
    抽出was extracted two times with diethyl ether
14. 14
    洗浄The combined ether layer was washed with saturated aqueous sodium chloride solution
15. 15
    乾燥dried over anhydrous magnesium sulfate
16. 16
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
17. 17
    その他The residue obtained

実験手順

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%

出典