Isopropanol → Benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanol

Temperature

-78 °C

A stirred mixture of 4-bromo-2-ethoxy-1-methoxy-benzene (1.74 g, 7.5 mmol) and dry THF (15 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (3.0 mL, 7.5 mmol) and stirred for 20 min. Then a mixture of benzofuran-5-carbaldehyde (1.0 g, 6.8 mmol) in dry THF (10 mL) was added and stirred for 1 hour at −78° C. The mixture was quenched with isopropanol (3.1 mL, 41 mmol) and added water (10 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organic phases were washed with water (2×50 mL), dried over MgSO4 and concentrated to give benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanol as an oil (2.36 g, 115% yield). The product was used in the next step without further purification.

1. customevacuated
2. additionrefilled with nitrogen for 10 cycles
3. additionwas added
4. stirringstirred for 1 hour at −78° C
5. extractionThe mixture was extracted with EtOAc (3×50 mL)
6. washThe combined organic phases were washed with water (2×50 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated

ORD record

ord-e1af349cfc3745339cd95e2a8fb40f99

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468446B2