Hexane → HCID 178506784, compound

Temperature

-20 °C

50 ml of ether were placed in a round-bottomed flask containing 1.68 g (0.023 moles) of cyclopentadienyllithium. After cooling of the reaction flask to −20° C., 3.6 g (0.023 moles) of chlorodiisopropylphosphine were added dropwise. When the addition was complete, the cooling bath was heated to 0° C. and the reaction mixture was stirred for 1 h. Ether was then removed under vacuum, the product was dissolved in toluene and the solution was filtered. After the frit had been rinsed with 2×10 ml of toluene, the reaction mixture was cooled to −20° C. and 9.3 ml of a 2.5 molar solution of butyllithium in hexane (0.023 moles) were added to form an orange coloured solution. A small fraction was taken for NMR studies and, after separation of the toluene under vacuum and washing of the resulting oil with hexane, a pale yellow solid (18) was obtained. 1H NMR (400 MHz, THF): δ=5.89 (m, 2H); 5.83 (bs, 2H); 1.86 (m, 2H); 1.0-0.8 (m, 12H).

1. additionWhen the addition
2. temperaturethe cooling bath was heated to 0° C.
3. customEther was then removed under vacuum
4. dissolutionthe product was dissolved in toluene
5. filtrationthe solution was filtered
6. washAfter the frit had been rinsed with 2×10 ml of toluene
7. temperaturethe reaction mixture was cooled to −20° C.
8. customto form an orange coloured solution
9. customafter separation of the toluene under vacuum
10. washwashing of the resulting oil with hexane

ORD record

ord-7f4aa61d7db14e249e4fb9c70373e013

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06433112B1