تفاعل #57067

معادلة التفاعل

MeOH

tetrabromo para-xylene

furan

BuLi

→

26

المردود 50.0%

5,6-Dibromo-4,7-dimethyl-1,4-epoxy-1,4-dihydronapthalene

المردود 50.0%

المذيبات

PhMe

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to rt
2. 2
   workup.WAITAfter 3 hours
3. 3
   أخرىThe organic layer was separated
4. 4
   استخلاصthe aqueous layer was extracted three times with Et2O
5. 5
   غسيلThe combined organic layers were washed with brine
6. 6
   تجفيفdried over MgSO4
7. 7
   تركيزconcentrated

الإجراء التجريبي

To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silca gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values. 22

المصدر