تفاعل #669936

معادلة التفاعل

sodium cyclopentadienylide

1-bromo-2-fluoroethane

sodium hydroxide

hydrogen peroxide

2-methyl-2-butene

→

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

المردود 16.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling and under nitrogen
2. 2
   أخرىThe resulting reaction liquid
3. 3
   ترشيحwas filtered with cerite, and the filtrate
4. 4
   workup.ADDITIONwas added under ice-
5. 5
   درجة الحرارةcooling and under nitrogen stream to a tetrahydrofuran solution of disiamylborane
6. 6
   أخرىprepared
7. 7
   workup.STIRRINGthe resulting mixture was stirred for 8 hours
8. 8
   درجة الحرارةcooling to the reaction liquid
9. 9
   أخرىobtained above, and the resulting mixture
10. 10
    workup.STIRRINGwas stirred for 1 hour
11. 11
    أخرىThe reaction liquid
12. 12
    أخرىthus obtained
13. 13
    استخلاصwas extracted two times with diethyl ether
14. 14
    غسيلThe combined ether layer was washed with saturated aqueous sodium chloride solution
15. 15
    تجفيفdried over anhydrous magnesium sulfate
16. 16
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
17. 17
    أخرىThe residue obtained

الإجراء التجريبي

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%

المصدر