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

HRID 224875

反応式

HRID 224875 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e810e93309c649d99782bfc28a9990d6
出典データセット
uspto-grants-1980_11
特許番号
US04234588

関連ノート

読み込み中…