Thionyl Chloride → HCID 87483165, compound

4.0 g (0.022 mol) of (R)-2-(4-hydroxyphenoxy)propionic acid was dissolved in 25 ml of thionyl chloride, the mixture was refluxed for 5 hours, and distilled under a reduced pressure. 3.3 g (0.016 mol) of (R)-2-(4-hydroxyphenoxy)propionic acid chloride thus obtained was dissolved in 60 ml of tetrahydrofuran, and the mixture was cooled to 0° C. 3.04 g (0.018 mol) of 2-amino-5-chlorobenzoxazole and triethylamine dissolved in 15 ml of tetrahydrofuran were sequentially added to the reaction mixture. The mixture was stirred at room temperature for 5 hours, and the solvent was removed therefrom under a reduced pressure. After adding water thereto, the mixture was extracted three times with ethyl acetate three times. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and distilled under a reduced pressure. The resulting residue was subjected to column chromatography (ethyl acetate:n-hexane=1:4) to obtain the title compound (4.04 g, 75.9%).

1. temperaturethe mixture was refluxed for 5 hours
2. distillationdistilled under a reduced pressure

ORD record

ord-e9866d9314ea47e2a557a446e6fbcc9b

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293774B2