But-3-enyl 4-methylbenzenesulfonate → gamma-Butenylcyclopentadiene

Temperature

0 °C

68.9 ml of a 2.0M solution of cyclopentadienyl sodium in tetrahydrofuran (THF) are added to a solution of 100 millimoles of the γ-butenyl 1-tosylate prepared in the preceding stage (a), in 200 ml of THF cooled to 0° C. The mixture is heated to ambient temperature (20° C.) and is stirred for 16 hours. 100 ml of an aqueous saline solution are added to the mixture and the product is extracted with ether (3′ 75 ml). The organic fractions are dried over magnesium sulphate for 2 hours, filtered and the solvents are removed at reduced pressure to give a dark brown oily crude product. The crude product is distilled at reduced pressure to give γ-butenylcyclopentadiene in the form of a colourless oil.

1. temperatureThe mixture is heated to ambient temperature (20° C.)
2. extractionthe product is extracted with ether (3′ 75 ml)
3. dry with materialThe organic fractions are dried over magnesium sulphate for 2 hours
4. filtrationfiltered
5. customthe solvents are removed at reduced pressure
6. customto give a dark brown oily crude product
7. distillationThe crude product is distilled at reduced pressure

ORD record

ord-9ea7b71300c14413ba177e91919a697c

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174972B1