Ethyl acetate hexane → HCID 22046522, compound

Participants

Reaction Steps

To a stirred solution of 1-Ethyl-1,2,3,4-tetrahydro-quinoline-3-carboxylic acid methyl ester (123 mg, 0.56 mmol) in 1.5 mL of Et2O at 0° C. under nitrogen. LAH (1M in Et2O) was added dropwise with vigorous gas evolution and a white precipitate formation. After 30 min., TLC in 3/7 EtOAc/hexane showed complete loss of s.m. and appearance of a clean lower rf spot. The reaction was carefully quenched with 15% NaOH (3 mL) and 3 mL of Et2O was added and the mixture stirred rapidly at RT for 15 min. The layers were separated and the aqueous layer extracted 1×10 mL with Et2O. The organics were combined, dried (MgSO4), filtered and concentrated to a clear oil corresponding to the desired alcohol (105 mg, 95%).

Provenance & Evidence