Ethyl Bromide → HCID 18357814, Verbindung

A mixed solution of 1-bromo-2-(2-tetrahydropyranyloxymethyl)benzene (2.71 g, 0.01 mol) and dry THF (8 ml) was added dropwise at 50° to 60° C. over 20 minutes to a solution prepared by adding dry THF (2 ml) and ethyl bromide (0.1 ml) to magnesium (0.36 g, 0.015 mol) in a stream of nitrogen. After completion of the addition, the mixture was stirred at 50° to 60° C. for 1 hour and cooled to room temperature. After cooling, the mixture was added dropwise to a mixed solution of oxalyl chloride (1.90 g, 0.015 mol) and dry THF (30 ml) at below -50° C. over 15 minutes. Then, the mixture was stirred at -60° to -70° C. for 40 minutes. A 40% methylamine-methanol solution (4.66 g, 0.06 mol) was added to the reaction mixture, and the mixture was stirred at -20° to -10° C. for 30 minutes. After completion of the reaction, water (150 ml) was added, and the mixture was extracted with ether (150 ml). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain N-methyl-2-oxo-2-[2-(2-tetrahydropyranyloxymethyl)phenyl]acetamide(1.18 g, Yield: 42.5%) as a colorless oil.

1. customprepared
2. additionAfter completion of the addition
3. temperatureAfter cooling
4. stirringThen, the mixture was stirred at -60° to -70° C. for 40 minutes
5. stirringthe mixture was stirred at -20° to -10° C. for 30 minutes
6. additionwas added
7. extractionthe mixture was extracted with ether (150 ml)
8. washThe extract was washed with saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

ORD-Eintrag

ord-6bbf1e87f26646bf9fea4edcf0230c5b

Quelldatensatz

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05856573