2-Methoxyethanol → 2-Chloro-4-(2-methoxyethoxy)pyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N:3]=1.[CH3:11][O:12][CH2:13][CH2:14][OH:15].CC([O-])(C)C.[K+]>>[Cl:1][C:2]1[CH:7]=[C:6]([O:15][CH2:14][CH2:13][O:12][CH3:11])[CH:5]=[CH:4][N:3]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 2-chloro-4-nitropyridine (43.6 g, 275.0 mmol) and 2-methoxyethanol (325.6 ml, 425 mmol) was cooled to 0° C. Potassium 2-methylpropan-2-olate (35.73 g, 302.5 mmol) was added and the resulting mixture was stirred while warming to ambient temp over 2 hours. The reaction mixture was concentrated under reduced pressure followed by dilution with 500 ml of water. The resulting mixture was extracted twice with 250 ml of dichloromethane. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure to produce the desired compound as a golden oil (50.2 g, 97% yield) MS APCI (+) m/z 188 and 189.9 (M+1 of each isotope) detected.
Workup
- temperaturewhile warming to ambient temp over 2 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- extractionThe resulting mixture was extracted twice with 250 ml of dichloromethane
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f76dbd2835ba4cd8a0e734a671fc31c4
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138181B2
Reaction notes
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