تفاعل #2268992

معادلة التفاعل

4-{[6-ethyl-2-(3-methoxyphenyl)phenanthridin-5(6H)-yl]sulfonyl}phenol

cyclohexene

boron tribromide

→

title compound

المردود 76.0%

3-{6-Ethyl-5-[(4-hydroxyphenyl)sulfonyl]-5,6-dihydrophenanthridine-2-yl}phenol

المردود 76.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGstirred for four hours
3. 3
   درجة الحرارةThe reaction was cooled to −30° C.
4. 4
   أخرىquenched with methanol (1 mL)
5. 5
   أخرىThe solvent was removed in vacuo
6. 6
   أخرىthe residue was purified by flash column chromatography on silica gel
7. 7
   غسيلeluting with a mixture of ethyl acetate-hexane (1:3)

الإجراء التجريبي

A stirred and cooled solution of 4-{[6-ethyl-2-(3-methoxyphenyl)phenanthridin-5(6H)-yl]sulfonyl}phenol (0.645 g, 1.36 mmol) and cyclohexene (1.1 mL, 10.9 mmol) in dichloromethane (5 mL) was treated drop-wise under nitrogen at −30° C. with boron tribromide (1.03 mL, 10.9 mmol). After the addition was completed, the reaction mixture was allowed to warm to room temperature and stirred for four hours. The reaction was cooled to −30° C. and quenched with methanol (1 mL). The solvent was removed in vacuo, and the residue was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:3); to yield the title compound (0.473 g, 1.03 mmol, 76%), which was characterized by LCMS (ES+, FA, CV=20 or 5), m.p. 105° C.;

المصدر