3-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinoline → HCID 178506786, compound

HRID 482977Notes

Reaction equation

HRID 482977 reaction equation
C([Li:5])CCC.[CH3:6][Si:7]([CH3:20])([CH3:19])[CH:8]1[C:17]2[N:16]=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH2:11][CH2:10][CH2:9]1>CCCCCC.C1COCC1>[Li:5][C:8]1([Si:7]([CH3:19])([CH3:20])[CH3:6])[C:17]2[N:16]=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 202445183-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinolineHCID 178418339Butyllithium

Product 1

HCID 178506786HCID 178506786, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A mixture of a solution of 1.5 molar n-butyl lithium in hexane (12.9 ml, 20 mM) and THF (10 ml), maintained at 5° was treated with a solution of 5,6,7,8-tetrahydro-8-trimethylsilyl-3-methylquinoline (4.34 g 20 mM) to obtain 5,6,7,8-tetrahydro-8-lithio-8- trimethylsilyl-3-methylquinoline. After 0.5 hour a solution of t-butyldimethylsilyl isothiocyanate (7.0 g 40 mM) was added and the mixture allowed to warm to 20° over 12 hours. The reaction was quenched with 2N hydrochloric acid and stirred 1 hour. The mixture was extracted with ether, the aqueous phase adjusted to pHlO and extracted with ether. The organic extracts were dried and evaporated to give the title compound (3 g, 85%) identical with authentic material.

Workup

  1. temperaturemaintained at 5°

Sources & evidence

ORD record
ord-de8a38a423df440a8fba92f36d143f39
Source dataset
uspto-grants-1986_03
Patent number
US04577022

Reaction notes

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