تفاعل #362816

معادلة التفاعل

8

(+)-2-Methyl-6-tert-butylindan-1-one

sodium borohydride

HCl

→

9

المردود 99.1%

2-Methyl-6-tert-butylindene

المردود 99.1%

المذيبات

tetrahydrofuran methanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added to pH 1
2. 2
   استخلاصthe mixture was extracted a number of times with diethyl ether
3. 3
   غسيلThe combined organic phases were washed with saturated aqueous NaHCO3 solution and NaCl solution
4. 4
   تجفيفdried (MgSO4)
5. 5
   أخرىThe solvent was removed in vacuo
6. 6
   أخرىthe crude product, without further purification
7. 7
   workup.ADDITION0.1 g of p-TsOH was added
8. 8
   درجة الحرارةthe mixture was refluxed for 1 hour
9. 9
   غسيلThe reaction mixture was washed with 100 ml of saturated aqueous NaHCO3 solution
10. 10
    أخرىthe solvent was removed in vacuo
11. 11
    ترشيحThe crude product was purified by filtration through 200 g of silica gel (hexane)

الإجراء التجريبي

5.3 g (26 mmol) of 8 were dissolved in 50 ml of tetrahydrofuran/methanol (2:1), 1.5 g of sodium borohydride were added at 0° C. with magnetic stirring, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was poured onto ice, conc. HCl was added to pH 1, and the mixture was extracted a number of times with diethyl ether. The combined organic phases were washed with saturated aqueous NaHCO3 solution and NaCl solution and dried (MgSO4). The solvent was removed in vacuo, and the crude product, without further purification, was taken up in 300 ml of toluene, 0.1 g of p-TsOH was added, and the mixture was refluxed for 1 hour. The reaction mixture was washed with 100 ml of saturated aqueous NaHCO3 solution, and the solvent was removed in vacuo. The crude product was purified by filtration through 200 g of silica gel (hexane), giving 4.8 g (99%) of 9 as a colorless oil.

المصدر