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Water → 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1,3-thiazole-2-carbaldehyde

HRID 1881824
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HRID 1881824 반응식
O1CC[O:3][CH:2]1[C:6]1[S:7][C:8]([CH:11]([OH:14])[CH2:12][OH:13])=[CH:9][N:10]=1.O.[C:16]1(C)[CH:21]=CC(S([O-])(=O)=O)=C[CH:17]=1.[NH+]1C=CC=CC=1>CC(C)=O>[CH3:17][C:16]1([CH3:21])[O:14][CH:11]([C:8]2[S:7][C:6]([CH:2]=[O:3])=[N:10][CH:9]=2)[CH2:12][O:13]1
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참가 물질

5

반응물 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2회HCID 593314951-[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]ethane-1,2-diol

생성물 1

HCID 593313925-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1,3-thiazole-2-carbaldehyde수율 113.3%

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

To a solution of 1-[2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]ethane-1,2-diol (1.50 g) in acetone (10 mL) were added water (1 mL) and pyridinium p-toluenesulfonate (0.52 g) and the mixture was stirred with heating under reflux overnight. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a crude product (1.20 g). To a solution of the obtained crude product (1.20 g) in acetone (80 mL) was added pyridinium p-toluenesulfonate (1.80 g), and the mixture was stirred with heating under reflux overnight. The reaction mixture was concentrated, the residue was dissolved in ethyl acetate, and the solution was washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (0.50 g, yield 34%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio). MS: 214 (MH+).

후처리

  1. temperaturewith heating
  2. temperatureunder reflux overnight
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give a crude product (1.20 g)
  8. stirringthe mixture was stirred
  9. temperaturewith heating
  10. temperatureunder reflux overnight
  11. concentrationThe reaction mixture was concentrated
  12. dissolutionthe residue was dissolved in ethyl acetate
  13. washthe solution was washed with water
  14. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  15. dry with materialdried (MgSO4)
  16. concentrationconcentrated

출처 및 근거

ORD 기록
ord-03a7cb53cf9b453eb4599cf67fee72b6
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318746B2

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