Nitrogen → 5-(4-Hydroxy-3-methylphenyl)-2-furanecarboxaldehyde

Pd(PPh3)4 (69.3 mg, 0.06 mmol) was added to a degassed (N2 for 15 min) solution of 4-bromo-2-methylphenol (225 mg, 1.20 mmol), 2-formylfuran-5-boronic acid (177 mg, 1.26 mmol) and aqueous 0.4 M Na2CO3 (6 mL) in MeCN (12 mL). The mixture was heated to reflux for 12 h. The hot mixture was filtered and the cake was washed with MeCN (6 mL). The filtrate was concentrated to half the volume and was diluted with EtOAc. The resulting solution was washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 7:3) to provide the title compound (115 mg, 47% yield) as a yellow solid.

1. temperatureThe mixture was heated
2. temperatureto reflux for 12 h
3. filtrationThe hot mixture was filtered
4. washthe cake was washed with MeCN (6 mL)
5. concentrationThe filtrate was concentrated to half the volume
6. additionwas diluted with EtOAc
7. washThe resulting solution was washed with water and brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by flash chromatography (Hexane:EtOAc, 7:3)

ORD-Eintrag

ord-b1aa848caddb427ab02d298633b3ab7b

Quelldatensatz

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06806265B2