Water → 2-(6-methoxy-1H-inden-3-yl)propanoic Acid

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Reaction Conditions

Reaction Steps

In a 1 L three-neck flask charged with NaOH (18.57 g, 0.464 mol) and water (216 mL), was slowly added (over 15-20 minutes) a solution of methyl 2-(6-methoxy-1H-inden-3-yl)propanoate (Example 8) (53.92 g, 0.232 mol) in MeOH (215 mL). During the addition, the reaction temperature increased to 38° C. To this mixture was added THF (108 mL), and then the mixture was heated to 40-45° C. for a period of 8 h and subsequently stirred at rt for 17 h. The solvent was removed under vacuum and the resulting aqueous mixture was extracted with CH2Cl2 (3×100 mL). The aqueous layer was acidified with HCl (38 mL, 37% aqueous solution) to pH ˜2.5 and extracted with EtOAc (3×100 mL). The combined organic layers were washed with water (4×150 mL) and brine (50 mL), dried over Na2SO4, and filtered. The solvent was evaporated under vacuum and the resulting oil was dried under vacuum at 40-45° C for 16-18 h to give 45.71 g (90%) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 7.25 (1H, d), 7.05 (1H, s), 6.83 (1H, dd), 6.19 (1H, s), 3.73 (3H, s), 3.68 (1H, q), 3.30 (2H, s), 1.39 (3H, d); LC-MS: RT=2.43 min, (M+H)+: 219.1.

Provenance & Evidence