Chlorotrimethylsilane → 4-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinoline

HRID 482973Notes

Reaction equation

[CH3:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH3:17][Si:18](Cl)([CH3:20])[CH3:19]>>[CH3:17][Si:18]([CH3:20])([CH3:19])[CH:7]1[C:6]2[N:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:11]=2[CH2:10][CH2:9][CH2:8]1

Participants

Reactant 3

HCID 6397Chlorotrimethylsilane

HCID 1856675,6,7,8-Tetrahydro-4-methylquinoline

HCID 178418339Butyllithium

Product 1

HCID 199746604-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinolineYield 95%

Procedure

The title compound was prepared in a similar manner to that described in Example 1 using 5,6,7,8-tetrahydro-4-methylquinoline (0.1 M), butyl lithium (0.11 M) and trimethylsilyl chloride (0.2 M) in 95% yield b.p. 80°/0.1 mm (Found: C71.1; H,9.3; N,6.0 C13N21NSi requires: C71.2; H,9.6; N,6.4%).

Sources & evidence

ORD record: ord-9da245c091544b77a698af113e8455f0
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04577022

Reaction notes

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