3-Acetylpyridine → ethyl (2Z)-3-(pyridin-3-yl)but-2-enoate

HRID 1719160노트

반응식

HRID 1719160 반응식
[Br-].[CH2:2]([O:4]C(C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)[CH3:3].[O-:27][CH2:28][CH3:29].[Na+].[C:31]([C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)(=O)[CH3:32]>C(O)C>[N:36]1[CH:37]=[CH:38][CH:39]=[C:34](/[C:31](/[CH3:32])=[CH:29]\[C:28]([O:4][CH2:2][CH3:3])=[O:27])[CH:35]=1

참가 물질

5

반응물 3

HCID 95893-AcetylpyridineHCID 73731(Ethoxycarbonylmethyl)triphenylphosphonium bromideHCID 2723922Sodium ethoxide

생성물 1

HCID 67402107ethyl (2Z)-3-(pyridin-3-yl)but-2-enoate수율 111.3%

시약·촉매·용매 1

HCID 702Ethanol용매3회

실험 절차

Ethoxycarbonylmethyltriphenylphosphonium bromide (100 g) in ethanol (500 ml) was added with stirring under nitrogen to a solution of sodium ethoxide (from 4.28 g sodium) in ethanol (100 ml). 3-Acetylpyridine (18.8 g) in ethanol (300 ml) was added dropwise over 0.5 hour. The mixture was allowed to stand for 14 days and was evaporated to dryness. The residue was taken up in water, the pH adjusted to 8.5 and the mixture was extracted with benzene. The extract was dried, evaporated and the residue was distilled at reduced pressure to give ethyl 3-(3-pyridyl)-crotonate (13.39 g) b.p. 78°/0.1 mmHg.

후처리

  1. customwas evaporated to dryness
  2. extractionthe mixture was extracted with benzene
  3. customThe extract was dried
  4. customevaporated
  5. distillationthe residue was distilled at reduced pressure

출처 및 근거

ORD 기록
ord-90f7b4e55d8a42bab5ae6b3654a39efb
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539207

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