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

HRID 1698230

반응식

HRID 1698230 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1d43c1f58a2542508d428f78f7318b7b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163918B2

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