Tetrahydrofuran → 9-[3-(Trichlorosilyl)propyl]-9H-carbazole

HRID 1045245Notes

Reaction equation

CN1C2C=CC([C:15]3[CH:16]=[CH:17][C:18]4[N:19]([CH2:42][CH:43]=[CH2:44])[C:20]5[C:25]([C:26]=4[CH:27]=3)=[CH:24][C:23](C3C=CC4N(C)C6C(C=4C=3)=CC=CC=6)=[CH:22][CH:21]=5)=CC=2C2C1=CC=CC=2.C1COCC1.[Cl:50][SiH:51]([Cl:53])[Cl:52]>C1(C)C=CC=CC=1>[Cl:50][Si:51]([Cl:53])([Cl:52])[CH2:44][CH2:43][CH2:42][N:19]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[C:26]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:27]=2

Participants

Conditions

Temperature: 60 °C

Procedure

To a three-neck flask fitted with a reflux condenser and a dropping funnel were added the 3,6-bis(9-methylcarbazol-3-yl)-9-allylcarbazole (10 g), anhydrous THF (100 g), and platinum (0) 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (250 mg of a 0.05% solution in anhydrous toluene). Then, trichlorosilane (30 g) was slowly added. When the addition of trichlorosilane was completed, the mixture was heated to 60° C. and maintained at that temperature for two hours. Then, the mixture was distilled at 0.02 torr to remove volatiles and gave 9-(3-trichlorosilylprop-1-yl)carbazole with a yield of about 5.6 g, at a concentration of about 90% by weight. 1 H NMR (CDCl3) δ 8.53 (d, 2 H, J=1.5 Hz); 8.46 (d, 2 H, J=1.2 Hz); 8.21 (d, 2 H, J=7.8 Hz); 7.87 (m, 4 H); 7.48 (m, 8 H); 7.27 (m, 2 H); 6.10 (m, 1 H); 5.40 (d, 1 H, J=9.0 Hz); 5.14 (d, 1 H, J=15.9 Hz); 5.00 (m, 2 H); 3.91 (s, 6 H).

Workup

customTo a three-neck flask fitted with a reflux condenser and a dropping funnel
temperaturemaintained at that temperature for two hours
distillationThen, the mixture was distilled at 0.02 torr
customto remove volatiles

Sources & evidence

ORD record: ord-fde34861446a48fd93b9e03cceaa8ea5
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08564871B2

Reaction notes

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