Reaktion #2163350

Reaktionsgleichung

calcium chloride

sodium borohydride

6-chloro-pyridine-2,5-dicarboxylic acid dimethyl ester

→

title compound

Ausbeute 69.2%

2-Chloro-6-hydroxymethyl-nicotinic acid methyl ester

Ausbeute 69.2%

Lösungsmittel

ethanol

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring at 0° C. for a further 6 hours
2. 2
   Sonstigethe reaction was quenched by the addition of H2SO4 (35 mL, 5M)
3. 3
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
4. 4
   Filtrationfiltered through Celite®
5. 5
   WaschenThe filtrate was washed with 1M NaOH, water and brine
6. 6
   Sonstigethe organic phase was isolated
7. 7
   Trocknendried (Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated in vacuo

Vorschrift

A cold (0° C.) suspension of calcium chloride (19.54 g, 176 mmol) and sodium borohydride (4.18 g, 110 mmol) in anhydrous ethanol (176 mL) and anhydrous THF (88 mL) was stirred for 1 hour, after which 6-chloro-pyridine-2,5-dicarboxylic acid dimethyl ester (9.97 g, 44 mmol) was added. After stirring at 0° C. for a further 6 hours, the reaction was quenched by the addition of H2SO4 (35 mL, 5M). The reaction mixture was diluted with ethyl acetate and filtered through Celite®. The filtrate was washed with 1M NaOH, water and brine, the organic phase was isolated, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si-PPC, gradient 0% to 100%, ethyl acetate in hexane) to afford the title compound as a yellow oil (6.14 g, 69%). LCMS (method B): RT=2.34 min, [M+H]+=202.

Quelle