Sodium Bicarbonate → 3-(5-Fluoro-pyridin-2-yl)-isoxazole-4-carbaldehyde

HRID 1923599노트

반응식

HRID 1923599 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[CH:11][O:10][N:9]=2)=[N:6][CH:7]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH:13]=[O:14])=[CH:11][O:10][N:9]=2)=[N:6][CH:7]=1

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 66643813[3-(5-Fluoro-pyridin-2-yl)-isoxazol-4-yl]-methanol

생성물 1

HCID 866472733-(5-Fluoro-pyridin-2-yl)-isoxazole-4-carbaldehyde수율 89.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of [3-(5-fluoro-pyridin-2-yl)-isoxazol-4-yl]-methanol (2.1 g, 10.8 mmol) in DCM (45 mL) was added a suspension of DMP (5.5 g, 13.0 mmol) in DCM (35 mL) portionwise and under Argon at room temperature and then the mixture was cooled to 0° C. and the resulting mixture warmed up to room temperature overnight. The mixture was then poured carefully into stirred saturated sodium hydrogen carbonate solution and the aqueous layer extracted with DCM. The combined organic layers were then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) gave the title compound (1.85 g, 89%) as a white solid. MS: m/e=193.1 [M+H]+.

후처리

  1. temperaturethe resulting mixture warmed up to room temperature overnight
  2. additionThe mixture was then poured carefully
  3. extractionthe aqueous layer extracted with DCM
  4. washThe combined organic layers were then washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-2b091751b08a4b53ab42676a4f0bef74
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178522B2

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