Cyclohexene → 3-[(3-Chloro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

A stirred suspension of 3-chloro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.38 g, 0.95 mmol) and cyclohexene (1.73 mL, 17.1 mmol) was treated dropwise at room temperature under nitrogen with a solution of 1.0 M boron tribromide (5.7 mL, 5.7 mmol) in dichloromethane. After stirring for 20 hours at room temperature, the reaction was quenched with a saturated, aqueous sodium bicarbonate solution (50 mL), and extracted with dichloromethane (6×20 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a crude residue. The crude residue was triturated with hexane and purified by flash column chromatography, eluting with a mixture of ethyl acetate-hexane (30:70), to afford the title compound as a homogeneous, white, crystalline solid (0.17 g, 73%), m.p. 215° C.;

1. customthe reaction was quenched with a saturated, aqueous sodium bicarbonate solution (50 mL)
2. extractionextracted with dichloromethane (6×20 mL)
3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo to a crude residue
6. customThe crude residue was triturated with hexane
7. custompurified by flash column chromatography
8. washeluting with a mixture of ethyl acetate-hexane (30:70)

ORDレコード

ord-cc29b6c262b44f47b45a3bc5c2ed9a19

出典データセット

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06894061B2