Toluene → HCID 71231031, compound

HRID 716477Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]=1[O:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][C:9]([CH3:25])=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.[Li]CCCC.[Cl:38][Si:39](Cl)([CH3:41])[CH3:40]>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]2[C:11]([CH:10]=[C:9]([CH3:25])[CH:8]2[Si:39]([Cl:38])([CH3:41])[CH3:40])=[C:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]=1[O:14][CH2:15][CH:16]([CH3:18])[CH3:17])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 16.8 g (50.2 mmol) of 5-tert-butyl-6-isobutoxy-2-methyl-7-phenyl-1H-indene in 200 ml of toluene 20.1 ml (50.5 mmol) of 2.5 M nBuLi in hexanes was added at room temperature. The formed viscous solution was stirred for 10 h, and then 10 ml of THF was added. The resulting mixture was stirred for 1 h at 65° C., then cooled to −20° C., and 32.5 g (252 mmol, 5 eq.) of dichlorodimethylsilane was added in one portion. This mixture was warmed to room temperature, refluxed for 0.5 h, and then filtered through glass frit (G3). The precipitate was additionally washed by 2×30 ml of toluene. The combined filtrate was evaporated to dryness to give 21.5 g (99%) of (6-tert-butyl-5-isobutoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane which was further used without an additional purification.

Workup

stirringThe resulting mixture was stirred for 1 h at 65° C.
temperatureThis mixture was warmed to room temperature
temperaturerefluxed for 0.5 h
filtrationfiltered through glass frit (G3)
washThe precipitate was additionally washed by 2×30 ml of toluene
customThe combined filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-b0902ee61b8642f7872e00a9c22e2165
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187583B2

Reaction notes

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