Dichlorodimethylsilane → HCID 21943872, compound

HRID 2425311Notes

Reaction equation

[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[C:8]([CH3:11])[CH:7]=[CH:6][C:5]=2[CH3:12].[Li]CCCC.CCCCCC.[Si:24]([CH3:28])([CH3:27])(Cl)[Cl:25]>CCOCC.C1COCC1>[Cl:25][Si:24]([CH:3]1[C:4]2[C:9](=[C:8]([CH3:11])[CH:7]=[CH:6][C:5]=2[CH3:12])[CH:10]=[C:2]1[CH3:1])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

7.24 g of 2,4,7 trimethylindene (45.8 mmol) were suspended in 70 ml of Et2O, cooled to 0° C., and to it were added 19.2 ml of a 2.5 M BuLi solution in hexane (48.0 mmol) with stirring. A slightly yellow cream is obtained. After allowing the reaction mixture to reach ambient temperature, additional 10 ml of Et2O were added, to improve stirring. After about 1 h the mixture was cooled again to 0° C. and 7.20 g of Me2SiCl2 (55.2 mmol, 1.2 eq) in 30 ml di THF, previously cooled to 0° C., were added to it. At the end of the addition, the reaction mixture was allowed to reach ambient temperature. At this point the reaction mixture, which appeared as a white suspension, was filtered to remove LiCl, and then all solvents and excess Me2SiCl2 were removed under reduced pressure to leave 11.8 g of pale yellow oil (98% yield).

Workup

customA slightly yellow cream is obtained
customto reach ambient temperature
stirringto improve stirring
temperatureAfter about 1 h the mixture was cooled again to 0° C.
additionwere added to it
additionAt the end of the addition
customto reach ambient temperature
filtrationwas filtered
customto remove LiCl
customall solvents and excess Me2SiCl2 were removed under reduced pressure

Sources & evidence

ORD record: ord-e7245a8d3da64edcabd0060a22589099
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964679B2

Reaction notes

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