Dimethylformamide → 3,5-Dimethylpyridine-4-carbaldehyde
Reaction equation
CON(C)C([C:6]1[CH:14]=[C:13]2C(C(C)=C[N:12]2[CH2:15][C:16]2[CH:21]=CC(OC)=[CH:18][CH:17]=2)=CC=1)=O.C([Li])CCC.CN(C)C=[O:34].[Cl-].[NH4+]>C(OCC)C>[CH3:21][C:16]1[CH:15]=[N:12][CH:13]=[C:14]([CH3:6])[C:17]=1[CH:18]=[O:34]Participants
Conditions
- Temperature
- -78 °C
Procedure
A stirred solution of 4-bromo-3,5-dimethylpyridine (3.72 g, Reference Example 25) in diethyl ether (50 ml), at −78° C. and under nitrogen, was treated dropwise with n-butyl lithium (0.025 ml, 1.6M). After stirring at −78° C. for 1 hour the resulting homogeneous solution was treated with dry dimethylformamide (6 ml) whilst maintaining the temperature below −65° C. The reaction mixture was allowed to warm to room temperature over 1 hour, then treated with a saturated aqueous solution of ammonium chloride (10 ml), and then extracted twice with ethyl acetate (100 ml). The combined extracts were evaporated to yield an orange oil which was subjected to flash chromatography on silica, eluting with a mixture of ethyl acetate and pentane (1:4, v/v) to afford the title compound (2.3 g) as a semi-solid.
Workup
- temperaturewhilst maintaining the temperature below −65° C
- temperatureto warm to room temperature over 1 hour
- extractionextracted twice with ethyl acetate (100 ml)
- customThe combined extracts were evaporated
- customto yield an orange oil which
- washeluting with a mixture of ethyl acetate and pentane (1:4, v/v)
Sources & evidence
- ORD record
- ord-17ee3eb85c804846a1e582d7e6e7e408
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07329675B2
Reaction notes
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