Water → 3-(2-Ethoxyethoxy)-2-methylpyridine

HRID 536090Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=1.[CH2:15]([O:17][CH2:18][CH2:19]Cl)[CH3:16].O>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([O:17][CH2:18][CH2:19][O:7][C:8]1[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

Potassium carbonate (2.20 g, 15.9 mmol) was added to a stirred solution of 3-hydroxy-2-methylpyridine (1.45 g, 13.3 mmol) and 2-chloroethyl ethyl ether (1.75 mL, 15.9 mmol) in DMF (7 mL) and the mixture was stirred at 70° C. overnight. The reaction was not complete and additional 2-chloroethyl ethyl ether (1 equiv.) and potassium carbonate (1 equiv.) were added and the mixture was stirred at 85° C. for 8 h. Water and ethyl acetate were added and the aqueous layer was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated. The crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 50% ethyl acetate), obtaining 1.80 g (75%) the title compound.

Workup

stirringthe mixture was stirred at 85° C. for 8 h
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 50% ethyl acetate)

Sources & evidence

ORD record: ord-03fed8b67ae14aaebbaee8f5a82c3451
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859568B2

Reaction notes

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