(3-(Piperidin-1-ylsulfonyl)phenyl)methanol → 3-(1-piperidinylsulfonyl)Benzaldehyde

HRID 1919857ノート

反応式

HRID 1919857 の反応式
[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH2:16][OH:17])[CH:13]=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(#N)C>[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[CH:16]=[O:17])(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

4

反応物 2

HCID 65750537(3-(Piperidin-1-ylsulfonyl)phenyl)methanolHCID 178418287HCID 178418287、化合物

生成物 1

HCID 212321303-(1-piperidinylsulfonyl)Benzaldehyde収率 81.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

A solution of (3-(piperidin-1-ylsulfonyl)phenyl)methanol (160 mg, 0.627 mmol) in acetonitrile (5 mL) was added dropwise over 3 minutes to a stirred, ice-cold solution of pyridinium chlorochromate (203 mg, 0.944 mmol) in acetonitrile (5 mL). On completion of the addition the mixture was allowed to attain room temperature, and then heated to reflux for 1 hour. After cooling to ambient temperature and concentrating in vacuo, the residue was then taken up with a mixture of ethyl acetate and saturated sodium bicarbonate solution. The biphasic mixture was transferred to a separating funnel and further partitioned using brine solution. The separated organic phase was passed through a short pad of silica gel, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford 3-(piperidin-1-ylsulfonyl)benzaldehyde (130 mg, 0.51 mmol, 81%) which was used directly without further purification.

後処理

  1. additionOn completion of the addition the mixture
  2. customto attain room temperature
  3. temperatureheated
  4. temperatureto reflux for 1 hour
  5. concentrationconcentrating in vacuo
  6. additionthe residue was then taken up with a mixture of ethyl acetate and saturated sodium bicarbonate solution
  7. customThe biphasic mixture was transferred to a separating funnel
  8. customfurther partitioned
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo

出典と根拠

ORDレコード
ord-9398480cc8b648ff917559d03e33c046
出典データセット
uspto-grants-2012_05
特許番号
US08168673B2

反応ノート

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