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

HRID 1923599ノート

反応式

HRID 1923599 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-2b091751b08a4b53ab42676a4f0bef74
出典データセット
uspto-grants-2012_05
特許番号
US08178522B2

反応ノート

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