4-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinoline → HCID 178506787, compound

HRID 482975Notes

Reaction equation

HRID 482975 reaction equation
C([Li:5])CCC.[CH3:6][Si:7]([CH3:20])([CH3:19])[CH:8]1[C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:18])[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][CH:14]=[C:13]([CH3:18])[C:12]=2[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 199746604-Methyl-8-(trimethylsilyl)-5,6,7,8-tetrahydroquinolineHCID 178418339Butyllithium

Product 1

HCID 178506787HCID 178506787, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A mixture of a 1.55 molar solution of n-butyl lithium in hexane (14.2 ml, 22mM) and THF (25 ml), maintained below 5° was treated with a solution of 5,6,7,8-tetrahydro-8-trimethylsilyl- 4-methylquinoline (4.4 g, 20 mM) in THF (10 ml) to give 5,6,7,8-tetrahydro-8-lithio-8-trimethylsilyl -4-methylquinoline. After 0.5 hour a solution of t-butyldimethylsilyl isothiocyanate (22 mM) in benzene (15 ml) was added; after a further 0.5 hour the mixture was quenched with 0.5 N hydrochloric acid (60 ml). After 1 hour toluene (50 ml) was added, the aqueous layer was separated, adjusted to pH10 and extracted with dichloromethane. The organic extract was evaporated and chromatographed on silica using ether as eluant. The title thioamide was obtained in 60% yield (identical to authentic material) together with the corresponding nitrile (20%) and 5,6,7,8-tetrahydro-4-methylquinoline (20%).

Workup

  1. temperaturemaintained below 5°

Sources & evidence

ORD record
ord-2e553916f4964ad580a0a842bc16360f
Source dataset
uspto-grants-1986_03
Patent number
US04577022

Reaction notes

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