Water → 5-[(2-Methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde

HRID 2226112Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6]Cl.[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[N:13][CH:14]=1.[H-].[Na+].O>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[N:13][CH:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

##STR94## A. Methoxyethoxymethyl chloride (MEM) (19 g, 153 mmol) was added to a solution of 5-hydroxy-2-pyridinecarboxaldehyde (18.4 g, 149 mmol)in 300 ml DMF. NaH (6.3 g of 60% oil dispersion, 158 mmol) were added in portions while cooling the mixture to maintain 20°-30° C. The mixture was stirred an additional 1 hour at 25° C. 5 ml water were added, most of the solvent was evaporated, and water was added to the residue. The mixture was extracted with EtOAc. The extracts were dried over Na2SO4, filtered, and evaporated to a residue. The residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65) to obtain 5-[(2-methoxyethoxy)methoxy]-2-pyridinecarboxaldehyde: C10H13NO4 (211.22); 1H-NMR (CDCl3) δ 10.01 (s,1), 8.52 (d,1), 7.93 (d,1), 7.49 (m,1), 5.39 (s,2), 3.80 (m,2), 3.53 (m,2), 3.32 (s,3).

Workup

temperaturewhile cooling the mixture
temperatureto maintain 20°-30° C
customwas evaporated
additionwater was added to the residue
extractionThe mixture was extracted with EtOAc
dry with materialThe extracts were dried over Na2SO4
filtrationfiltered
customevaporated to a residue
customThe residue was chromatographed on silica gel eluting with EtOAc-hexanes (35:65)

Sources & evidence

ORD record: ord-b1c9c425531f428bbb46db50ef838610
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05346898

Reaction notes

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