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

HRID 1921334노트

반응식

HRID 1921334 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7bace05600ac4233a4b51c51e6c5b04f
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

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