Ethyl Bromide → HCID 68841469, Verbindung

A mixture of ethyl bromide (30.0 g, 0.3 mole) and 3-bromopyridine (16.0 g, 0.1 mole) was added dropwise to magnesium powder (10.0 g) in diethyl ether (50 ml). After the Grignard reaction had gone to completion, 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (10.5 g, 47.6 mmole) in THF (80 ml) was added within 15 minutes at 0° C. to the grey solution and the mixture was stirred overnight at RT. 20% ammonium chloride solution (50 ml) and water (50 ml) were then added to the reaction solution while cooling with ice. The reaction solution was diluted with diethyl ether (100 ml), and the organic phase was separated and the aqueous phase was extracted twice with Et2O (100 ml). The combined organic phases were washed with water (50 ml) and NaCl solution (50 ml), dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was taken up in 2-butanone (200 ml) and Me3SiCl (10 ml) was added at 0° C. The reaction solution was stirred for 5 hours under exclusion of moisture and the precipitated solid was suction filtered.

1. customAfter the Grignard reaction
2. additionwas added within 15 minutes at 0° C. to the grey solution
3. temperaturewhile cooling with ice
4. customthe organic phase was separated
5. extractionthe aqueous phase was extracted twice with Et2O (100 ml)
6. washThe combined organic phases were washed with water (50 ml) and NaCl solution (50 ml)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customthe solvent was removed in vacuo
10. additionMe3SiCl (10 ml) was added at 0° C
11. stirringThe reaction solution was stirred for 5 hours under exclusion of moisture
12. filtrationfiltered

ORD-Eintrag

ord-0c32783ac96b48eb8cf2d32cad505376

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08399503B2