2-Methoxy-4,6-dimethylnicotinaldehyde → 2-Methoxy-4,6-dimethyl-3-vinylpyridine

HRID 1921334Notes

Reaction equation

HRID 1921334 reaction equation
[CH3:1]C(C)([O-])C.[K+].CP(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:27][C:28]1[CH:33]=[C:32]([CH3:34])[N:31]=[C:30]([O:35][CH3:36])[C:29]=1[CH:37]=O>C1(C)C=CC=CC=1>[CH3:36][O:35][C:30]1[C:29]([CH:37]=[CH2:1])=[C:28]([CH3:27])[CH:33]=[C:32]([CH3:34])[N:31]=1

Participants

5

Reactant 3

HCID 108558412-Methoxy-4,6-dimethylnicotinaldehydeHCID 23665647Potassium tert-butoxideHCID 178503019methyl(triphenyl)-lambda5-phosphane

Product 1

HCID 674925022-Methoxy-4,6-dimethyl-3-vinylpyridineYield 55.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Potassium tert-butoxide (1.63 g, 14.54 mmol) is added to a suspension of methyl triphenylphosphine (5.20 g, 14.54 mmol) in toluene (70 mL) and the mixture is stirred at room temperature of 0.5 hr. To this yellow-orange mixture is added a solution of 4,6-dimethyl-2-methoxypyridine-3-carbaldehyde (1.20 g, 7.27 mmol) in toluene (10 mL). After 1.5 hr. the reaction mixture is washed with water (150 mL), with brine (150 mL), dried, filtered and concentrated and the residue is purified by chromatography eluting with cyclohexane-5% ethyl acetate. Product containing fractions are combined and concentrated to afford 2-methoxy-4,6-dimethyl-3-vinylpyridine (0.66 g, 55.5% yield) as an oil containing triphenylphosphine oxide.

Workup

  1. waitAfter 1.5 hr
  2. washthe reaction mixture is washed with water (150 mL), with brine (150 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue is purified by chromatography
  7. washeluting with cyclohexane-5% ethyl acetate
  8. additionProduct containing fractions
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7bace05600ac4233a4b51c51e6c5b04f
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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