تفاعل #81149

معادلة التفاعل

alcohol

3-(tert-butyldimethylsilyloxy)-1-(3,4-dichlorophenyl)-2-butanol

ethyl ether

sodium hydride

2-naphthylmethyl bromide

→

4-(3,4- dichlorophenyl)-3-(2-naphthylmethoxy)-2-butanol

المردود 18.5%

المذيبات

water

tetrahydrofuran

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةunder cooling with ice
3. 3
   workup.STIRRINGThe mixture was stirred at the same temperature for 30 minutes
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature for 20 hours
5. 5
   غسيلThe organic layer was washed with a saturated sodium chloride aqueous solution
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   أخرىThe drying agent was separated by filtration
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   أخرىThe residue was subjected to silica gel column chromatography (hexane→hexane/ethyl acetate=50/1) for rough purification
10. 10
    workup.ADDITIONadded to a liquid mixture of 100 me of tetrahydrofuran and 8 me of a 1M tetrahydrofuran solution of tetrabutylammonium fluoride
11. 11
    workup.STIRRINGThe mixture was stirred at room temperature for 3 hours
12. 12
    تركيزThe reaction solution was concentrated under reduced pressure
13. 13
    استخلاصThen, the residue was extracted by an addition of ethyl acetate and water
14. 14
    غسيلThe organic layer was washed with a saturated sodium chloride aqueous solution
15. 15
    تجفيفdried over anhydrous magnesium sulfate
16. 16
    أخرىThe drying agent was separated by filtration
17. 17
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

الإجراء التجريبي

2.32 g of the alcohol compound thus obtained was dissolved in a liquid mixture of 100 ml of tetrahydrofuran and 20 ml of dimethylformamide, and 0.34 g of 60% oily sodium hydride was added thereto with stirring under cooling with ice. The mixture was stirred at the same temperature for 30 minutes. Then, 1.47 g of 2-naphthylmethyl bromide was added thereto, and the mixture was stirred at room temperature for 20 hours. Then, ethyl ether and water were added to the reaction solution for liquid separation. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane→hexane/ethyl acetate=50/1) for rough purification and then added to a liquid mixture of 100 me of tetrahydrofuran and 8 me of a 1M tetrahydrofuran solution of tetrabutylammonium fluoride. The mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure. Then, the residue was extracted by an addition of ethyl acetate and water. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=20/1→5/1) to obtain 0.46 g (yield: 18%) of 4-(3,4- dichlorophenyl)-3-(2-naphthylmethoxy)-2-butanol.

المصدر