Triacetoxyperiodinane → 1-tosyl-1H-pyrazole-4-carbaldehyde

HRID 559731

反応式

HRID 559731 の反応式
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[N:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1.C([O-])(O)=O.[Na+]>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[C:13]([CH:15]=[O:16])[CH:12]=[N:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

参加物

5

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 59278506[1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol

生成物 1

HCID 577430311-tosyl-1H-pyrazole-4-carbaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of [1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-methanol (5.20 g, 20.61 mmol) in THF was added Dess-Martin periodinane (15.00 g, 35.37 mmol). After 3 hours, the mixture was diluted with saturated aqueous NaHCO3 and filtered through diatomaceous earth. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 20-50% ethyl acetate in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford 1-(toluene-4-sulfonyl)-1H-pyrazole-4-carbaldehyde.

後処理

  1. filtrationfiltered through diatomaceous earth
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with a gradient of 20-50% ethyl acetate in heptane
  7. concentrationthe solvent was concentrated in vacuo

出典と根拠

ORDレコード
ord-790e87c37cbb42d1ae92ecf6ea4f61b6
出典データセット
uspto-grants-2011_11
特許番号
US08063065B2

関連ノート

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