Malonic Acid → 3-(2-Pyridyl)acrylic acid

HRID 2307412ノート

反応式

HRID 2307412 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12]>N1C=CC=CC=1.N1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:10][C:11]([OH:13])=[O:12]

参加物

5

反応物 2

HCID 867Malonic AcidHCID 142732-Pyridinecarboxaldehyde

生成物 1

HCID 2478243-(2-Pyridyl)acrylic acid

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 31268Pyrrolidine溶媒

実験手順

A mixture of pyridine-2-carboxaldehyde (32.1 g 0.30 mmol), malonic acid (62.4 g, 0.60 mmol) in pyridine (200 mL) and pyrrolidine (2 mL) was stirred under reflux for 16 hours. The reaction mixture was allowed to cool to room temperature and poured into ice water (200 mL). The aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic layer was concentrated in vacuo and the crude material obtained was purified by flash column chromatography on silica using a gradient system of solvents: 1) ethyl acetate (100%); 2) methanol/ethyl acetate (10%). The title product was obtained (6.28 g, 14%) as a grayish-green solid.

後処理

  1. temperatureunder reflux for 16 hours
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×100 mL)
  3. concentrationThe combined organic layer was concentrated in vacuo
  4. customthe crude material obtained
  5. customwas purified by flash column chromatography on silica using a gradient system of solvents

出典と根拠

ORDレコード
ord-1cb936644af94698b65ff833e07b01ef
出典データセット
uspto-grants-2004_12
特許番号
US06831080B2

反応ノート

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