Ethyl 5-(4-Aminophenyl)-2-Methyl-3-Furoate → Ethyl 5-(4-hydroxyphenyl)-2-methyl-3-furanecarboxylate

A solution of NaNO2 (111 mg, 1.61 mmol) in water (1 mL) was added over 5 min to an ice-cold suspension of ethyl 5-(4-aminophenyl)-2-methyl-3-furanecarboxylate (395 mg, 1.61 mmol) in aqueous 1 M H2SO4 solution (12 mL). The reaction mixture was stirred at 0° C. for 20 min then was heated to 90° C. for 1 h. The cooled mixture was extracted with EtOAc. The organic layer was washed with water (2×) and brine, dried (MgSO4), filtered and concentrated under reduced pressure to yield the title compound (78 mg, 20% yield) as a white solid.

1. temperaturethen was heated to 90° C. for 1 h
2. extractionThe cooled mixture was extracted with EtOAc
3. washThe organic layer was washed with water (2×) and brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD record

ord-371b50119d0c4c279cf533262f1fe6ab

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06806265B2