Pyridine → Isopropyl 2-methoxy-1-naphthoate

Temperature

0 °C

To a solution of 2-methoxynaphthoic acid (458 mg, 2.3 mmol) in dry dichloromethane (9 mL) at 0° C. under a N2 atmosphere was added oxalyl chloride (1.4 mL of a 2M solution in dichloromethane, 2.8 mmol) and 4 drops of N,N-dimethyl formamide. The mixture was stirred at 0° C. for 20 minutes then allowed to warm to room temperature and stirred for one hour. The mixture was concentrated in vacuo. To this dry powder was added isopropanol (9 mL) and pyridine (367 μL, 4.5 mmol), with stirring. After stirring for 2 hours at room temperature, the mixture was concentrated and partitioned between H2O (10 mL) and ethyl acetate (3× 10 mL) and the combined organic layers was washed with saturated NaCl (10 mL). The organic layer was dried over Na2SO4, and the crude product was purified by column chromatography on silica gel using 10% ethyl acetate in hexane. The title compound was obtained as a colorless solid (260 mg, 47%).

1. temperatureto warm to room temperature
2. stirringstirred for one hour
3. concentrationThe mixture was concentrated in vacuo
4. stirringwith stirring
5. stirringAfter stirring for 2 hours at room temperature
6. concentrationthe mixture was concentrated
7. custompartitioned between H2O (10 mL) and ethyl acetate (3× 10 mL)
8. washthe combined organic layers was washed with saturated NaCl (10 mL)
9. dry with materialThe organic layer was dried over Na2SO4
10. customthe crude product was purified by column chromatography on silica gel using 10% ethyl acetate in hexane

ORD record

ord-3f0a47e72f234e2b844744c7afd38f7e

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538105B2