5,6,7,8-Tetrahydro-8-trimethylsilyl-3-methylquinoline → HCID 178506786, compound

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

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.