Sodium hydride → 5-(Cyclobutoxymethyl)benzofuran

Temperatur

0 °C

A mixture of cyclobutanol (1.0 mL, 14.0 mmol) and sodium hydride (0.5 g, 14.0 mmol) in DMF (20 mL) was stirred at 0° C. for 30 minutes. 5-(Bromomethyl)benzofuran (2.9 g, 14.0 mmol) was the added and resultant reaction mixture was slowly warmed to room temperature and left stirring over night. Reaction mixture was diluted to 100 mL with water. The solution was extracted with Et2O (20 mL×3); the combined extracts were washed with 1N NaOH solution, water and brine, dried, and concentrated under reduced pressure to yield the desired product after purification on silica (4/1 hexane/ethyl acetate). 1H NMR (400 MHz, CDCl3) δ 7.58 (d, 2H), 7.42 (d, 1H), 7.27 (d, 1H), 6.78 (s, 1H), 4.54 (s, 2H) 4.03 (m, 1H), 2.21 (m, 2H), 1.94 (m, 2H), 1.76 (m, 1H), 1.52 (m, 1H).

1. additionadded
2. customresultant reaction mixture
3. temperaturewas slowly warmed to room temperature
4. waitleft
5. stirringstirring over night
6. customReaction mixture
7. extractionThe solution was extracted with Et2O (20 mL×3)
8. washthe combined extracts were washed with 1N NaOH solution, water and brine
9. customdried
10. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-70d071907057470e94b8d4c591bb2261

Quelldatensatz

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07919519B2