Hydrochloric Acid → HCID 22614989, compound

Participants

Reaction Conditions

Reaction Steps

4-(3-Bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (27.3 g), the compound in Example 5-a, was dissolved in THF (546 ml) and cooled at 0° C. To the solution were added LiOH.H2O (6.72 g), water (410 ml) and MeOH (135 ml). The mixture was stirred at room temperature for seven hours. To the reaction mixture was added 1N-HCl (133 ml). After evaporating the organic solvent, the mixture was mixed with ethyl acetate (1,400 ml). The organic layer was dried over anhydrous sodium sulfate and evaporated to give colorless needles. The colorless needles were washed with ethyl acetate-hexane (2:8) to obtain pure 4-(3-bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid (28.3 g). FAB-MS: m/z 312 (M+); 1H-NMR (CDCl3): δ 2.43 (2H, quintet, J=6.5 Hz), 2.78 (3H, s), 3.66 (2H, t, J=6.5 Hz), 4.25 (2H, t, J=6.5 Hz), 6.67 (1H, d, J=8 Hz), 7.17 (1H, d, J=8 Hz), 7.38 (1H, t, J=8 Hz).

Provenance & Evidence