Water → (4-Nitrobenzofuran-2-yl)methanol

Temperature

80 °C

2-Iodo-4-nitrophenol (30 mg, 0.11 mmol) and propargyl alcohol (19 mg, 0.33 mmol) were suspended in a mixture of water (1 ml) and acetonitrile (0.2 ml). Triethylamine (34.3 mg, 0.34 mmol), Pd/C (10%, 2.6 mg, 5.6 μmol), triphenylphosphine (5.9 mg, 22.6 μmol) and copper iodide (2.15 mg, 11.3 μmol) were then added and the heterogeneous mixture was heated at 80° C. while stirring for 3 hours. After cooling the reaction mixture was filtered over celite, and a mixture of water (40 ml) and ethyl acetate (20 ml) was added to the filtrate. After separation of the phases the aqueous phase was extracted with ethyl acetate (2×10 ml) and the combined organic phase was washed with a saturated solution of NaHCO3, then brine, dried over Na2SO4 and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel flash chromatography to give 17.2 mg of pure 4-nitro-benzofuran-2-yl-methanol (78% yield).

1. temperatureAfter cooling the reaction mixture
2. filtrationwas filtered over celite
3. additiona mixture of water (40 ml) and ethyl acetate (20 ml)
4. additionwas added to the filtrate
5. customAfter separation of the phases the aqueous phase
6. extractionwas extracted with ethyl acetate (2×10 ml)
7. washthe combined organic phase was washed with a saturated solution of NaHCO3
8. dry with materialbrine, dried over Na2SO4
9. customthe solvent was evaporated under reduced pressure
10. customThe crude product was purified by silica gel flash chromatography

ORD record

ord-f48eb5843f6945749e6198a8b83a7102

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795255B2