Hydrochloric Acid → HCID 66896793, compound

Participants

Reaction Conditions

Reaction Steps

3-[3-(3,5-Di-iso-propyl-2-methoxymethoxyphenyl)-benzo[b]thien-5-yl]-but-2-enoic acid methyl ester (15 mg, 0.033 mmol) (see Example 55, step F) was dissolved in MeOH (2 ml) and 1N NaOH (2 ml). The mixture was then stirred at 60° C. for 2 h, then cooled to ambient temperature and brought to pH 2 with 1N HCl . The reaction mixture was allowed to stir for 1 h, it was extracted with ethyl acetate (3×5 mL) and the organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography (10% ethyl acetate in hexanes) to give 3-[3-(2-hydroxy-3,5-diisopropyl-phenyl)-benzo[b]thien-5-yl]-but-2-enoic acid as a white solid (11.7 mg, 89%). 1H NMR (250 MHz, CDCl3): δ 7.89 (d, 1H, J=8.75), 7.70 (d, 1H, J=0.62), 7.50 (m, 2H), 7.08 (d, 1H, J=1.2), 6.95 (d, 1H, J=1.2), 6.14 (bs, 1H), 3.29 (m, 1H), 2.85 (m, 1H), 2.55 (s, 3H), 1.27 (s, 3H), 1.25 (s, 3H), 1.23 (s, 3H), 1.20 (s, 3H). MS [EI+] 395 (M+H−H2O)+, [EI−] 393 (M−1)−. HPLC [MetaSil AQ C18 (0.46×25 cm) 95% CH3CN(0.1% TFA) in H2O(0.1% TFA)] 4.388 min.

Provenance & Evidence