6-Isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde → 6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde (Intermediate 7, 2.00 g, 9.00 mmol) and 35 ml of anhydrous THF under argon at −78° C. was slowly added 3 M solution of methyl magnesium bromide in THF (7.5 ml, 22.5 mmol). The resulting solution was stirred at −78° C. for 45 minutes. The reaction was quenched with saturated NH4Cl and the product was extracted with diethyl ether. The organic extract was washed with water, and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography using 5% ethyl acetate in hexane to yield the title compound as light yellow oil.

Provenance & Evidence