Triethylamine → HCID 58046344, compound

To a solution of 2-methoxy-4-(trifluoromethoxy)benzaldehyde (1.0 g, 4.542 mmol) in dichloromethane (15 mL) was added m-chloroperoxybenzoic acid (2.04 g, 9.08 mmol). The resulting clear solution was stirred for 16 hours at room temperature. A white precipitate had formed and this was filtered off. The filtrate was evaporated to a white solid, which was diluted with ethyl acetate (25 mL) and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulphate, and evaporated to a white solid. This solid was redissolved in methanol (15 mL), and treated with triethylamine (2 mL, 10 mmol). After stirring for two hours, the solvents were evaporated. The residue was taken up in ethyl acetate (25 mL), and washed with 1N citric acid solution (20 mL) and brine (20 mL) dried over sodium sulphate, and evaporated to an oil. This crude material was then purified by eluting through a short pad of silica with dichloromethane, which afforded the title compound as a clear oil (650 mg, 57%)

1. customA white precipitate had formed
2. filtrationthis was filtered off
3. customThe filtrate was evaporated to a white solid, which
4. additionwas diluted with ethyl acetate (25 mL)
5. washwashed with saturated aqueous sodium bicarbonate
6. dry with materialThe organic layer was dried over sodium sulphate
7. customevaporated to a white solid
8. dissolutionThis solid was redissolved in methanol (15 mL)
9. stirringAfter stirring for two hours
10. customthe solvents were evaporated
11. washwashed with 1N citric acid solution (20 mL) and brine (20 mL)
12. dry with materialdried over sodium sulphate
13. customevaporated to an oil
14. customThis crude material was then purified
15. washby eluting through a short pad of silica with dichloromethane, which

ORD record

ord-82134e80000b4e5595dca4bad2fdf92c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685977B2