4-Isopropoxybenzoic acid → 4-[5-(4-Isopropoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-phenylmethanol

Temperatur

140 °C

A solution of 4-iso-propoxybenzoic acid (2.0 g, 11.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.13 g, 11 mmol), 1-hydroxybenzotriazole hydrate (1.50 g, 11.1 mmol) and DMF (14 mL) was stirred at room temperature for 30 minutes. N-hydroxyl-4-(hydroxylmethyl)benzamidine (1.84 g, 11.1 mmol) was added to the reaction mixture and stirred at 140° C. for 2 hours. The reaction mixture was cooled to room temperature, quenched with water (20 mL) and the aqueous layer was extracted with EtOAc (100 mL). The combined organic layers were washed with 1N HCl and sat. NaHCO3, dried (Na2SO4), filtered and concentrated in vacuo to provide the title compound (2.0 g, 58% yield) as a pale yellow solid.

1. temperatureThe reaction mixture was cooled to room temperature
2. customquenched with water (20 mL)
3. extractionthe aqueous layer was extracted with EtOAc (100 mL)
4. washThe combined organic layers were washed with 1N HCl and sat. NaHCO3
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD-Eintrag

ord-224ae29159e0485a92ae5945c9663dba

Quelldatensatz

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07671043B2