Glycol monoethyl ether → 3-Ethoxy-4-(2-ethoxyethoxy)-2-methylpyridine
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:22][C:23]1[C:28](=[O:29])[CH:27]=[CH:26][NH:25][C:24]=1[CH3:30])[CH3:21].[CH2:31]([O:33][CH2:34][CH2:35]O)[CH3:32].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:20]([O:22][C:23]1[C:24]([CH3:30])=[N:25][CH:26]=[CH:27][C:28]=1[O:29][CH2:32][CH2:31][O:33][CH2:34][CH3:35])[CH3:21]Participants
6
Procedure
Triphenylphosphine (2.93 g, 11.2 mmol) was added to a stirred solution of 3-ethoxy-2-methylpyridin-4(1H)-one (1.42 g, 9.3 mmol, obtained from Example 4(b)) in THF (15 mL). 2-Ethoxy ethanol (2.93 g, 11.2 mmol) was added dropwise, followed by dropwise addition of DEAD (1.76 mL, 11.2 mmol). The reaction mixture was then stirred under reflux overnight. The solvent was evaporated in vacuo and the residue was dissolved in water (15 mL). The aqueous solution was adjusted to pH 1 with 2M hydrochloric acid, then extracted with ethyl acetate (3×20 mL). The combined organic phases were dried (MgSO4) and concentrated, and the crude product was purified by flash chromatography (CHCl3/MeOH; 9:1), giving the title compound (0.92 g, 44%).
Workup
- temperatureunder reflux overnight
- customThe solvent was evaporated in vacuo
- dissolutionthe residue was dissolved in water (15 mL)
- extractionextracted with ethyl acetate (3×20 mL)
- dry with materialThe combined organic phases were dried (MgSO4)
- concentrationconcentrated
- customthe crude product was purified by flash chromatography (CHCl3/MeOH; 9:1)
Sources & evidence
- ORD record
- ord-2b1283cf42044842b3660b8ef27fb0c8
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026244B2
Reaction notes
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