Water → Methyl 3-bromotetrahydrofuran-3-carboxylate

温度

-78 °C

5.0 g (38.419 mmol) of methyl tetrahydrofuran-3-carboxylate (Journal of Organic Chemistry; 1996; 2690) were dissolved in 200 ml of THF and cooled to −78° C., and 76.83 ml (76.83 mmol) of bis(trimethylsilyl)lithium amide (1 M in THF) were then added. After 30 min at −78° C., 10.26 g (57.63 mmol) of N-bromosuccinimide, suspended in 50 ml of THF, were added slowly. The mixture was then allowed to warm to RT overnight. Water was added, and the mixture was extracted with ethyl acetate. The phases were separated and the aqueous phase was extracted two more times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution and then dried with sodium sulphate, filtered and concentrated. The crude product was purified by chromatography on silica gel (mobile phase:dichloromethane). This gave 491 mg (6% of theory) of the title compound.

1. additionwere added slowly
2. temperatureto warm to RT overnight
3. extractionthe mixture was extracted with ethyl acetate
4. customThe phases were separated
5. extractionthe aqueous phase was extracted two more times with ethyl acetate
6. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
7. dry with materialdried with sodium sulphate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified by chromatography on silica gel (mobile phase:dichloromethane)

ORDレコード

ord-0395be5644a54735823ecbdc4f2a9c5e

出典データセット

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09216978B2