Water → 6-(4-Fluoro-benzyloxy)-pyridine-2,3-dicarboxylic acid diethyl ester

HRID 431588Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1.[CH2:12]([O:14][C:15]([C:17]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=[C:19](Cl)[N:18]=1)=[O:16])[CH3:13].O>O1CCCC1>[CH2:12]([O:14][C:15]([C:17]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=[C:19]([O:9][CH2:8][C:7]2[CH:10]=[CH:11][C:4]([F:3])=[CH:5][CH:6]=2)[N:18]=1)=[O:16])[CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of sodium hydride (55% in mineral oil, 254 mg, 0.6 mmol) and 4-fluorobenzylalcohol in tetrahydrofuran (30 mL) was heated at 60° C. for 30 min and then after cooling at 0° C. a solution of 6-chloro-pyridine-2,3-dicarboxylic acid diethyl ester (1.3 g. 0.5 mmol) in tetrahydrofuran (20 mL) was added over 10 min. The resulting mixture was kept at 0° C. for 1 h and then water was added. The mixture was then extracted with ethylacetate and the combined organic extracts washed with water, brine and then dried over sodium sulfate. Filtration and evaporation gave a residue which was purified by chromatography (SiO2, heptane-EtOAc 9:1 to 3:1) to afford the title compound (1.3 g, 74%) as a colorless oil. MS: m/e=348.4 (M+H+).

Workup

additionwas added over 10 min
extractionThe mixture was then extracted with ethylacetate
washthe combined organic extracts washed with water, brine
dry with materialdried over sodium sulfate
filtrationFiltration and evaporation
customgave a residue which
customwas purified by chromatography (SiO2, heptane-EtOAc 9:1 to 3:1)

Sources & evidence

ORD record: ord-bfb7280eb78a45e7913cc4301ca8cd75
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660736B2

Reaction notes

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