Tetrahydrofuran → HCID 58706315, compound
Reaction equation
C([Li])CCC.[CH:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=O.[Cl-].[NH4+].[C:16](OCC)(=[O:18])C.[CH2:22]1[CH2:26][O:25]C[CH2:23]1>>[CH2:10]([O:11][C:12]1[CH:23]=[C:22]([CH:26]=[O:25])[CH:6]=[N:8][C:13]=1[O:18][CH3:16])[CH3:9]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of the 5.28 g of light yellow oil in 80 ml of THF there was added dropwise 9.07 ml of n-butyllithium (2.64 M, hexane solution) at −78° C. over a period of 20 minutes. After stirring at −78° C. for 3 hours, 4.59 ml of N-formylmorpholine was added. After further stirring at −78° C. for 20 minutes, the temperature was slowly allowed to rise to room temperature. Saturated aqueous ammonium chloride was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to give 5-ethoxy-6-methoxypyridine-3-carbaldehyde (2.23 g) as a light yellow oil.
Workup
- stirringAfter further stirring at −78° C. for 20 minutes
- customto rise to room temperature
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe desiccating agent was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate)
Sources & evidence
- ORD record
- ord-4f4d44e77883416fb5a7c5aaac407bfb
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816522B2
Reaction notes
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