Indene → HCID 131734356, compound
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15]>>[CH:11]([C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1)=[CH:12][CH2:13][CH2:14][CH3:15]Participants
Procedure
Metallocene MET-1, shown below, was synthesized by first reacting lithiated indene with 5-bromo-1-pentene. Pure 3-(1-pentenyl) indene was obtained via vacuum distillation as a pale yellow oil. One mole of 3-(1-pentenyl) indene was added to diethyl ether and cooled to −74° C., and one mole of n-butyllithium was added. The reaction mixture was stirred at 21° C. for 3 hr, then cooled again to −74° C., followed by the addition of a diethyl ether solution of dichloro(diisopropylamino) boron, and then stirred for 12 hr while warming to 21° C. The resulting yellow slurry was centrifuged, and the bright yellow solution was poured off and solvent removed under reduced pressure. Monochloro(diisopropylamino)-3-(1-pentenyl)indenylboron was obtained as a yellow oil. 1 mol of indene was added to diethyl ether and cooled to −74° C., then n-butyllithium was added and the solution was stirred at 20° C. for 3 hr. The solution was cooled to −74° C. and a diethyl ether solution of monochloro(diisopropylamino)-3-(1-pentenyl)indenylboron was added, resulting in an orange slurry, which was stirred at 20° C. for 12 hr. The reaction solution was filtered into a Schlenk-tube and the solvent was removed under reduced pressure, yielding Ligand-1 shown below.
Workup
- customwas synthesized
Sources & evidence
- ORD record
- ord-796991e6234d43d4a02b2533aaa1fd25
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303110B2
Reaction notes
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