2-Methyl-2-butene → 4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}-3-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}-3-methylbenzaldehyde (50 mg, 0.11 mmol) synthesized in Example 51 was dissolved in a mixed solvent of t-butanol (5.0 mL) and water (2.0 mL), and 2-methyl-2-butene (0.15 mL, 1.42 mmol) and sodium dihydrogen phosphate dihydrate (80 mg, 0.51 mmol) were added, followed by slow addition of sodium chlorite (25 mg, 0.28 mmol) at 0° C. and stirring at 0° C. for 2 hours under nitrogen atmosphere. An aqueous sodium hydrogen sulfite solution (5 mL) was added at 0° C., and stirring was carried out at room temperature for 10 minutes. An aqueous sodium hydrogen sulfite solution (15 mL) was added, and extraction was carried out with ethyl acetate (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to afford the desired compound (58 mg, yield ˜100%) as a yellow solid.

Provenance & Evidence