2-Methoxyethanol → 5-(2-Methoxyethoxy)pyridine-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].[CH3:12][O:13][CH2:14][CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:15][CH2:14][O:13][CH3:12])=[CH:7][N:6]=1)=[O:4]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a precooled solution of 5-hydroxy-pyridine-2-carboxylic acid methyl ester (CAS registry 30766-12-2) (150 mg, 0.980 mmol) and 2-methoxyethanol (82 mg, 0.085 ml, 1.077 mmol) in THF (10 ml) was added at 0° C. triphenylphosphine (397 mg, 1.469 mmol) and the reaction mixture was stirred for 10 min at 0° C. A solution of DIAD (316 mg, 1.469 mmol) in THF (5 ml) was added and the mixture was stirred at room temperature for 19.5 h. After dilution with EtOAc, the crude mixture was extracted with water and brine, the aqueous layers were reextracted with EtOAc, the combined organic extracts dried over Na2SO4, filtered and the filtrate concentrated to yield the title compound after flash chromatography on silica gel (DCM/EtOAc gradient 0-3 min 60:40; 3-35 min 60:40 to 25:75).
Workup
- stirringthe mixture was stirred at room temperature for 19.5 h
- extractionAfter dilution with EtOAc, the crude mixture was extracted with water and brine
- dry with materialthe combined organic extracts dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate concentrated
Sources & evidence
- ORD record
- ord-1ce7ebe4d4fd4e08b67114449cc5caf3
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846658B2
Reaction notes
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