Dimethylformamide → 3,5-Dimethylpyridine-4-carbaldehyde

HRID 380421Notes

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-5fae81e151c04f1f90e15cffa23c488f
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303600B1

Reaction notes

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