تفاعل #317472

معادلة التفاعل

water

n-butyllithium

1,4-diiodobenzene

Tetrahydro-4H-pyran-4-one

→

tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe resulting mixture was stirred at −78° C. for 1.5 hours
2. 2
   workup.STIRRINGAfter stirring the mixture for another 3 hours at room temperature
3. 3
   استخلاصthe resulting mixture was extracted with ethyl acetate
4. 4
   غسيلOrganic layer was washed once with water and once with saturated brine
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   أخرىAfter removing anhydrous sodium sulfate
7. 7
   ترشيحby filtration
8. 8
   تركيزthe filtrate was concentrated
9. 9
   أخرىThe residue was recrystallized from cyclohexane/ethyl acetate mixed solvent

الإجراء التجريبي

Under an argon atmosphere, a solution of n-butyllithium (2.59M, in hexane) (8.76 ml) was added dropwise to a solution of 1,4-diiodobenzene (7.49 g) in anhydrous THF (50 ml) at −78° C., and the resulting mixture was stirred at −78° C. for 30 minutes. Tetrahydro-4H-pyran-4-one (2.09 ml) was added dropwise thereto and the resulting mixture was stirred at −78° C. for 1.5 hours. After stirring the mixture for another 3 hours at room temperature, water was added, and the resulting mixture was extracted with ethyl acetate. Organic layer was washed once with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was recrystallized from cyclohexane/ethyl acetate mixed solvent to obtain tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol (4.12 g).

المصدر