Methanol → HCID 18521185, compound

First, the intermediate product 2,3-diphenylnorbornadiene was prepared as follows: A solution of 2,3-bis(tert-butylsulfonyl)norbornadiene (prepared according to the procedure of Riera, et al. Tetrahedron Letters 1990, volume 31, page 2173) (5.50 g, 19 mmol) in dry tetrahydrofuran (50 mL) was treated with 95 mmol of phenyl lithium at −78° C. under an argon atmosphere. After allowing the reaction mixture to gradually warm to room temperature overnight, methanol (25 mL) was added, and the solution was partially concentrated at reduced pressure. The resulting mixture was mixed with water (50 mL) and extracted with dichloromethane (2×50 mL). The combined organic extracts were dried over magnesium sulfate and concentrated to deposit a brown oil. The intermediate product was purified by column chromatography (silica gel, hexane/dichloromethane), followed by recrystallization from methanol to provide 1.25 g (27% yield) of 2,3-diphenylnorbornadiene as a white solid. 1H NMR (CDCl3) δ2.10 (m, 1 H), 2.40 (m, 1 H), 3.92 (m, 2 H), 7.01 (t, 2 H), 7.2-7.3 (m, 10 H).

1. customFirst, the intermediate product 2,3-diphenylnorbornadiene was prepared
2. concentrationthe solution was partially concentrated at reduced pressure
3. additionThe resulting mixture was mixed with water (50 mL)
4. extractionextracted with dichloromethane (2×50 mL)
5. dry with materialThe combined organic extracts were dried over magnesium sulfate
6. concentrationconcentrated
7. customThe intermediate product was purified by column chromatography (silica gel, hexane/dichloromethane)
8. customfollowed by recrystallization from methanol

ORD record

ord-e6a426512d2342aeb59ee4b21fcee674

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06569600B2