Selenium Dioxide → HCID 58478784, 화합물

HRID 1011340노트

반응식

HRID 1011340 반응식
[CH3:1][C:2]1[N:7]=[C:6]2[CH2:8][O:9][C:10](=[O:11])[C:5]2=[CH:4][CH:3]=1.[Se](=O)=[O:13]>O1CCOCC1>[O:11]=[C:10]1[C:5]2[C:6](=[N:7][C:2]([CH:1]=[O:13])=[CH:3][CH:4]=2)[CH2:8][O:9]1

참가 물질

4

반응물 2

HCID 24007Selenium Dioxide2회HCID 58478770HCID 58478770, 화합물

생성물 1

HCID 58478784HCID 58478784, 화합물수율 80%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A solution of 2-methyl-7H-furo[3,4-b]pyridin-5-one (1.41 g, 9.46 mmol) in dioxane (50 mL) is treated with selenium dioxide (1.2 g, 10.8 mmol) and the reaction mixture is heated at 100° C. for 3 h. Additional selenium dioxide (1.2 g, 10.8 mmol) is added at 3 and 6 hours and the reaction mixture is heated at 100° C. The reaction is heated at 100° C. for an additional 42 h. The reaction mixture is filtered through celite and washed with dioxane. The filtrate is concentrated under reduced pressure and subject to chromatography (silica gel, EtOAc/hexane). The high Rf product containing fractions are concentrated to give 5-Oxo-5,7-dihydro-furo[3,4-b]pyridine-2-carbaldehyde (1.23 g, 80%). The low Rf containing fractions are concentrated to give 5-Oxo-5,7-dihydro-furo[3,4-b]pyridine-2-carboxylic acid (159 mg, 9%).

후처리

  1. temperaturethe reaction mixture is heated at 100° C
  2. temperatureThe reaction is heated at 100° C. for an additional 42 h
  3. filtrationThe reaction mixture is filtered through celite
  4. washwashed with dioxane
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. additionThe high Rf product containing fractions
  7. concentrationare concentrated

출처 및 근거

ORD 기록
ord-b3240599312a472aad325e45839a5afc
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977351B2

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