Methyl 2-pyridylacetate → 3-Ethylindolizine-1-carboxylic acid

HRID 1638974ノート

反応式

HRID 1638974 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10]C)=[O:9].Br[CH:13]([CH2:16][CH3:17])[CH:14]=O>C1(C)C(C)=CC=CC=1>[CH2:16]([C:13]1[N:1]2[C:2]([CH:3]=[CH:4][CH:5]=[CH:6]2)=[C:7]([C:8]([OH:10])=[O:9])[CH:14]=1)[CH3:17]

参加物

4

反応物 2

HCID 74264Methyl 2-pyridylacetateHCID 126178112-Bromobutanal

生成物 1

HCID 147882723-Ethylindolizine-1-carboxylic acid

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A solution of methyl 2-pyridylacetate (6 ml) 2,6-lutidine (6 ml) and 2-bromobutyraldehyde (5.5 g) (P. Duhamel, L. Duhamel, J-Y. Valnot, Bull. Soc. Chim. Fr. 1973(4) 1465) in xylene (200 ml) was heated under reflux overnight, removing water by means of a Dean and Stark apparatus. The reaction mixture was cooled, washed with dilute citric acid solution and the organic phase dried (Na2SO4) and concentrated. Column chromatography (SiO2, CH2Cl2) of the residue afforded the methyl ester of the title compound (4.6 g). A solution of the ester (4.6 g) in EtOH (100 ml) and 1N NaOH (50 mL) was heated under reflux for 3h. The reaction mixture was cooled, the EtOH evaporated and the aqueous residue washed with Et2O (50 mL). Acidification of the aqueous layer afforded the title compound (3.0 g).

後処理

  1. temperatureunder reflux overnight
  2. customremoving water by means of a Dean and Stark apparatus
  3. temperatureThe reaction mixture was cooled
  4. washwashed with dilute citric acid solution
  5. dry with materialthe organic phase dried (Na2SO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-9b10047a9b424a62b4354124a25f22a2
出典データセット
uspto-grants-1989_11
特許番号
US04882327

反応ノート

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