Sodium, 2,4-cyclopentadien-1-yl- → 2-methoxyethylcyclopentadiene

Temperature

0 °C

To a solution of 19.7 g(85.7 mmol) 2-methoxyethyltosylate as prepared in step (a) in 200 ml THF cooled to 0° C. was added 55 ml of 2.0M (110 mmol) sodium cyclopentadienylide in THF. The reaction mixture was allowed to warm to room temperature and was stirred for 16 h. 100 ml concentrated aqueous saline solution was added and the product extracted with diethyl ether (3×75 ml). The combined organic fractions were dried over sodium sulphate for 16 hrs, filtered and the solvents removed under reduced pressure using a rotary evaporator to yield a brown oil. The crude product was distilled under reduced pressure (b.p. 40°-44° C. at 2-3 mm Hg) to give 4.5 g of a colourless oil (37.7 mmol, 44.0%).

1. temperatureto warm to room temperature
2. extractionthe product extracted with diethyl ether (3×75 ml)
3. dry with materialThe combined organic fractions were dried over sodium sulphate for 16 hrs
4. filtrationfiltered
5. customthe solvents removed under reduced pressure
6. customa rotary evaporator
7. customto yield a brown oil
8. distillationThe crude product was distilled under reduced pressure (b.p. 40°-44° C. at 2-3 mm Hg)

ORD record

ord-8055b98a2beb48a09a6df63a9510aaf6

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05767209