Ammonium Chloride → Sodium Methoxide

Temperature

-78 °C

A 4.37 M sodium methoxide solution was prepared by dissolving sodium metal (2.10 g, 91.4 mmol) in dry methanol (20 ml). In a separate flask, Bestmann's reagent (2.11 ml, 13.5 mmol) was taken up in THF (44.3 ml) and cooled to −78° C. The sodium methoxide solution (3.09 ml, 13.50 mmol) was added dropwise to the reaction mixture over 30 minutes. A solution of 6-chloro-2-methylnicotinaldehyde (1.00 g, 6.43 mmol) in THF (20 ml) and then added dropwise to the reaction over 30 minutes and the reaction was allowed to warm slowly to −10° C. and maintained at −10° C. for 90 minutes. Saturated aqueous ammonium chloride was added, the layers were separated and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to afford the title compound.

1. temperatureto warm slowly to −10° C.
2. temperaturemaintained at −10° C. for 90 minutes
3. customthe layers were separated
4. extractionthe aqueous layer was extracted three times with ethyl acetate
5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. custompurified by silica gel chromatography (0-50% ethyl acetate/hexanes)

ORD record

ord-bf3f58b1027e4c08946d1641515aef51

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2