Chlorotrimethylsilane → 3-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinoline

HRID 482972Notes

Reaction equation

HRID 482972 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.C([Li])CCC.[CH3:17][Si:18](Cl)([CH3:20])[CH3:19]>CCCCCC.O1CCCC1>[CH3:17][Si:18]([CH3:20])([CH3:19])[CH:6]1[C:5]2[N:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:10]=2[CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 1200283-Methyl-5,6,7,8-tetrahydroquinolineHCID 178418339Butyllithium

Product 1

HCID 202445183-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinolineYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

A mixture of 5,6,7,8-tetrahydro-3-methylquinoline (29.4 g, 0.2 M) and tetrahydrofuran (THF) (50 ml) was added to a mixture of a 1.55 molar solution of butyl lithium in hexane (129 ml, 0.2 M) and THF (50 ml), maintained below 10°. After 0.5 hour the mixture was blown over by inert gas onto a mixture of trimethylsilyl chloride (50 ml, 0.4 M) in the THF (100 ml), maintained below 10°. After 0.5 hour, the mixture was evaporated and the residue extracted with hexane. The hexane extracts were evaporated with the residue distilled to give the title compound (40 g, 91%) b.p. 118°-124°/5 mbar. (Found: C70.9; H,9.65; N,6.4% C13H21NSi requires: C,71.2; H,9.6; N6.4%).

Workup

  1. temperaturemaintained below 10°
  2. temperaturemaintained below 10°
  3. customthe mixture was evaporated
  4. extractionthe residue extracted with hexane
  5. customThe hexane extracts were evaporated with the residue
  6. distillationdistilled

Sources & evidence

ORD record
ord-78a9d0b885624a679eb568879c81147d
Source dataset
uspto-grants-1986_03
Patent number
US04577022

Reaction notes

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