Sodium Bicarbonate → (2S)-2-{3-[5-(4,5-Dihydro-1,3-oxazol-2-yl)-1H-pyrrol-2-yl]-5-[4-(methyl sulfonyl)phenoxy]phenoxy}propan-1-ol

Temperature

-78 °C

2-(5-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-4,5-dihydro-1,3-oxazole (3.17 g, 6.74 mmol) synthesized in Example 20 was dissolved in dichloromethane (100 mL), and cooled to −78° C., and a 1.0 mol/l boron tribromide dichloromethane solution (7.07 mL, 7.07 mmol) was added under nitrogen atmosphere. The temperature was raised naturally, followed by stirring at room temperature for 30 minutes, subsequently a saturated aqueous sodium hydrogencarbonate solution was added to neutralize the reaction solution, and extraction was carried out with dichloromethane (200 mL). The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with ethyl acetate (100 mL) and ethanol (50 mL) to afford the desired product (1.96 g, yield 64%) as a white solid.

1. temperatureThe temperature was raised naturally
2. extractionthe reaction solution, and extraction
3. washThe organic layer was washed with saturated brine
4. dry with materialsubsequently dried over sodium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. washthe resulting residue was washed with ethyl acetate (100 mL) and ethanol (50 mL)

ORD record

ord-3b99bd0f2cdb4266acea14e70a2c0e1b

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017610B2