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

HRID 1921334ノート

反応式

HRID 1921334 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 674925022-Methoxy-4,6-dimethyl-3-vinylpyridine収率 55.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7bace05600ac4233a4b51c51e6c5b04f
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

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