Chlorotrimethylsilane → (2-Dimethylaminoethyl)cyclopentadienyltrimethylsilane

HRID 1738588Notes

Reaction equation

[CH3:1][N:2]([CH3:10])[CH2:3][CH2:4][C:5]1CC=CC=1.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].Cl[Si:17](C)([CH3:19])[CH3:18].[CH2:21]1COCC1>>[CH3:1][N:2]([CH3:10])[CH2:3][CH2:4][CH2:5][Si:17]([CH:14]1[CH:21]=[CH:11][CH:12]=[CH:13]1)([CH3:19])[CH3:18]

Participants

Reactant 4

HCID 6397Chlorotrimethylsilane

HCID 8028Tetrahydrofuran

HCID 12154709(N,N-dimethylaminoethyl)cyclopentadiene

HCID 178418339Butyllithium

Product 1

HCID 131721397(2-Dimethylaminoethyl)cyclopentadienyltrimethylsilaneYield 89%

Procedure

Treatment of (2-dimethylaminoethyl) cyclopentadiene (32.24 g, 236 mmol) with n-butyllithium (148 ml, 1.6M in hexane) in THF (150 ml) at 0° C. and subsequent reaction with chlorotrimethylsilane (30 ml, 236 mmol) at 0° C. for 4 hours followed by filtration of the precipitate, removal of the volatiles, and distillation at reduced pressure (51-52° C., 5×10-3 mm Hg) afforded at least three isomers of (2-dimethylaminoethyl)cyclopentadienyltrimethylsilane as a pale yellow liquid (44.12 g, 89%). 1H NMR (CDCl3) 8 6.70-6.05 (m, ring H), 3.28 (br s, ring H), 3.07-2.85 (m, ring H), 2.65-2.37 (m, 4H, CH2CH2N(CH3)2), 2.28 (s, major isomer), 2.27 (s) [6H, N(CH3)2 ], 0.14 (s), 0.13 (s), -0.04 (s, major isomer).

Workup

filtrationfollowed by filtration of the precipitate, removal of the volatiles, and distillation at reduced pressure (51-52° C., 5×10-3 mm Hg)

Sources & evidence

ORD record: ord-cb3d713b2142440a8360d61b6b2fd965
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05962714

Reaction notes

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