Chlorotrimethylsilane → HCID 20675487, compound

HRID 1387758Notes

Reaction equation

[CH3:1][C:2]1[CH:3]([CH2:11][CH:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[C:13]2[CH3:21])[C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Li]CCCC.CCCCCC.Cl[Si:34]([CH3:37])([CH3:36])[CH3:35]>CCOCC>[CH3:21][C:13]1[CH:12]([CH2:11][CH:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]([Si:34]([CH3:37])([CH3:36])[CH3:35])=[C:2]2[CH3:1])[C:20]2[C:15]([C:14]=1[Si:34]([CH3:37])([CH3:36])[CH3:35])=[CH:16][CH:17]=[CH:18][CH:19]=2

Participants

Conditions

Temperature: -50 °C

Procedure

6.32 g of bis(2-methyl-1-indenyl)methane (23.2 mmol) were dissolved in 70 ml Et2O in a 250 ml Schlenk tube, and the white suspension was cooled to −50° C. 19.5 ml of 2.5 M BuLi in hexane (48.8 mmol) were added dropwise over 20 minutes under stirring. The suspension was allowed to warm to room temperature and stirred for 3 hours. The final suspension was light yellow. 6.2 ml of chlorotrimethylsilane (48.8 mmol) were dissolved in 50 ml Et2O. The two mixtures were both cooled to −50° C. and the Li salt suspension in Et2O was added to the chlorotrimethylsilane solution in Et2O. The cooling bath was removed and the reaction mixture was stirred overnight at room temperature. Then the reaction mixture, colored in yellow, was quenched with a few ml of MeOH, filtered and concentrated, thus giving 9.36 g of an brown and viscous liquid (96.8% yield).

Workup

temperatureto warm to room temperature
stirringstirred for 3 hours
temperatureboth cooled to −50° C.
customThe cooling bath was removed
stirringthe reaction mixture was stirred overnight at room temperature
customThen the reaction mixture, colored in yellow, was quenched with a few ml of MeOH
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-c93bfa1905ea4c309d9ced05027934dd
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268518B1

Reaction notes

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