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

HRID 2307412노트

반응식

HRID 2307412 반응식
[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]

참가 물질

5

반응물 2

HCID 867Malonic AcidHCID 142732-Pyridinecarboxaldehyde

생성물 1

HCID 2478243-(2-Pyridyl)acrylic acid

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 31268Pyrrolidine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1cb936644af94698b65ff833e07b01ef
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06831080B2

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