6-Methoxy-2-pyridinecarboxaldehyde → 2-Methoxy-6-vinylpyridine

HRID 2178511Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][O:7][C:8]1[N:13]=C(C=O)C=[CH:10][CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH:3]([C:2]1[CH:1]=[CH:10][CH:9]=[C:8]([O:7][CH3:6])[N:13]=1)=[CH2:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of methyl(triphenyl)phosphonium bromide (7.07 g, 19.8 mmol, 1.1 eq) in dry THF (50 ml) at 0° C. is added n-butyl lithium (1.6M in cyclohexane, 12.5 ml, 19.8 mmol, 1.1 eq). After stirring at 0° C. for 20 minutes, a solution of 6-methoxypyridine-2-carbaldehyde a1-50 (2.5 g, 18 mmol, 1 eq) in dry THF (10 ml) is added dropwise to the mixture. The reaction mixture is warmed to room temperature for 30 minutes. The reaction mixture is quenched with 3 drops of water, and Rochelle salt is added (10 g). The mixture is filtered on Celite and MgSO4. The crude residue is distilled to afford 400 mg of pure 2-ethenyl-6-methoxypyridine a1-51.

Workup

temperatureThe reaction mixture is warmed to room temperature for 30 minutes
customThe reaction mixture is quenched with 3 drops of water, and Rochelle salt
additionis added (10 g)
filtrationThe mixture is filtered on Celite and MgSO4
distillationThe crude residue is distilled

Sources & evidence

ORD record: ord-27c50c947368461192f9f61d41c234f1
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067930B2

Reaction notes

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