Methanol → 3-{5-[1-Hydroxy-3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-thiophen-2-yl}-2-methyl-2-phenoxy-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A sample of 2-methyl-3-{5-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propionyl]-thiophen-2-yl}-2-phenoxy-propionic acid methyl ester (1.00 g, 2.04 mmol) was dissolved in THF (40 mL) and MeOH (20 mL) and cooled to 0° C. Sodium borohydride (115 mg, 3.06 mmol) was added and allowed to stir at 0° C. for 45 min. The reaction was monitored by HPLC. Upon the completion of the reaction, the bulk of the solvent was removed in vacuo and water (40 mL) was added. The mixture was acidified with 6 N HCl (20 mL) and stirred for 30 min. This aqueous mixture was then extracted with CH2Cl2 (2×50 mL). The organic fractions were combined, dried over NaCl, and solvent removed in vacuo to give a crude oil. Flash chromatography (gradient 20% to 40% EtOAc in hexane) provided 650 mg (65%) of desired product: 1H NMR (400 MHz, CDCl3) δ 8.02 (d, 2 H), 7.47 (m, 3 H), 7.19 (m, 2 H), 6.96 (t, 1 H), 6.79 (m, 3 H), 6.68 (d, 2 H), 4.96 (m, 1 H), 3.72 (s, 3 H), 3.43 (d, 1 H), 3.29 (d, 1 H), 2.71 (m, 2 H), 2.30 (s, 3 H), 2.17 (m, 2 H), 1.42 (s, 3 H); MS (EI) 492.2 (M+H)+.

Provenance & Evidence