Methyl chloroformate → Methyl 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate
Reaction equation
[Li][C:2]1([Si](C)(C)C)[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.Cl[C:18]([O:20][CH3:21])=[O:19]>C1COCC1>[CH3:21][O:20][C:18]([CH:2]1[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1)=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
8-Lithio-5,6,7,8-tetrahydro-3-methyl-8-trimethylsilylquinoline, prepared as in Example 3, is treated with 1 equivalent of methyl chloroformate in THF at -20° C. under nitrogen. After the addition the mixture is allowed to warm to ambient temperature and the solvent removed by evaporation. The residue is dissolved in 2NHCl and washed with ether basified with Na2CO3 and extracted with chloroform. The extracts are dried and evaporated. Distillation of the residue gives the title compound as a pale yellow oil bp 120°/0.25 mm.