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

Temperature

0 °C

To a solution of 26.0 g (101 mmol) tetrahydrofurfuryltosylate prepared according to step (a) above in 200 ml THF cooled to 0° C. was added 63 ml of 2.0M (126 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 then added to the mixture and the product extracted with diethyl ether (3×75 ml). The combined organic fractions were dried over sodium sulphate for 16 h, 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. 32°-34° C. at 0.3-0.4 mm Hg) to give 7.1 g of a colourless oil (47.3 mmol, 46.9%).

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 h
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. 32°-34° C. at 0.3-0.4 mm Hg)

ORD record

ord-8ead4cf4f396485396b32a97d7c74365

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05767209