Water → 7-Allyl-6-methoxy-2-methylbenzoxazole

Temperature

190 °C

1.04 g of 2′-allyloxy-4′-methoxyacetanilide was dissolved in 20 ml of 1-methyl-2-pyrrolidone. The reaction solution was then stirred while heating at 190° C. under nitrogen atmosphere. Eight hours later, the reaction solution was stood to cool. Thereafter, water and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The obtained organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, so as to obtain a product (1.01 g). The obtained product was dissolved in 20 ml of acetic acid without purification, and the obtained solution was stirred while heating at 135° C. After completion of the reaction, the reaction solution was stood to cool. Thereafter, the solvent was concentrated under a reduced pressure. 5 N NaOH and ethyl acetate were added to the residue, so as to separate an organic layer. The obtained organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was then purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 371 mg of the subject compound.

1. customEight hours
2. temperatureto cool
3. customso as to separate an organic layer
4. washThe obtained organic layer was washed with a saturated sodium chloride solution
5. dry with materialdried over anhydrous magnesium sulfate
6. customAfter removing the drying agent
7. filtrationby filtration
8. concentrationthe organic layer was concentrated under a reduced pressure

ORD record

ord-9e91ab42a4d54f85b6478b9b87a8e048

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538123B2