Hexane → 3-Ethoxy-4-methoxybenzaldehyde

To a solution of 5-bromo-2,3-dihydro-benzofuran (1.0 g, 5.0 mmol) in THF (10 mL) was added a solution of n-butyllitium in hexane (1.8 mL, 2.5 N, 4.5 mmol) at −78° C. and kept for 20 min. To the mixture was added a solution of 3-ethoxy-4,N-dimethoxy-N-methyl-benzamide (1.1 g, 4.6 mmol) in THF (10 mL) at −78° C. After 30 min, isopropanol (1 mL) and water (10 mL) was added to the mixture, and the cold bath was removed. The mixture was stirred at room temperature for 20 min. The mixture was extracted with ethyl acetate (50 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers was washed with HCl (1N, 50 mL), water (50 mL), brine (50 mL) and dried over MgSO4. Removal of solvent and gave 2,3-dihydro-benzofuran-5-yl)-(3-ethoxy-4-methoxy-phenyl)-methanone as an oil (1.23 g, 92% yield). The oil was used in the next step without further purification.

1. waitAfter 30 min
2. customthe cold bath was removed
3. extractionThe mixture was extracted with ethyl acetate (50 mL) and water (50 mL)
4. extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
5. washThe combined organic layers was washed with HCl (1N, 50 mL), water (50 mL), brine (50 mL)
6. dry with materialdried over MgSO4
7. customRemoval of solvent

ORD record

ord-a0151f278c1e44da8c12d347ae4fbfca

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468446B2