Dimethylformamide → HCID 58497917, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-1-naphtoic acid tert-butyl ester (Example 9.2) (6.1 g) in dry tetrahydrofuran (54 ml) cooled to −100° C. was added a solution of butyl lithium (1.6M in hexane) (12.5 ml) dropwise at −100° C., followed by addition of dimethyl-formamide (“DMF”) (2.77 ml) at −100° C. The reaction mixture was stirred at −95° C. for 75 minutes. The reaction was quenched by addition of aqueous ammonium chloride (saturated) (8 ml) at −90° C. The mixture was stirred for 10 minutes at −90° C., warmed to 0° C. and poured onto a mixture of ice and water. The mixture was allowed to warm to ambient temperature and then extracted twice with ethyl acetate. The combined organic extracts were washed with water, dried over sodium sulfate and concentrated to give 5-formyl-1-naphtoic acid tert-butyl ester (3 g) as yellow oil. 1H-NMR (CDCl3, 400 MHz): 10.35 (s, 1H), 9.50 (s, 1H), 9.18 (d, 1H), 8.15 (d, 1H), 8.00 (d, 1H), 7.65-7.75 (m, 2H), 1.65 (s, 9H).

Provenance & Evidence