Acetone → Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide

HRID 231343노트

반응식

HRID 231343 반응식
[S:1]1(=[O:9])(=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]([OH:7])[CH2:2]1.CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>C(O)(C)C>[S:1]1(=[O:9])(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 13567415Tetrahydro-2H-thiopyran-3-ol 1,1-dioxideHCID 131709961Jones' reagent

생성물 1

HCID 11815935Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide수율 67.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a solution of tetrahydrothiopyran-3-ol-1,1-dioxide (7.5 g, 0.05 moles) and acetone (150 mL) was slowly added enough Jones reagent to maintain a brown color for at least 10 minutes without need for additional reagent. The excess reagent was reduced by addition of isopropanol (5 mL). The mixture was filtered through anhydrous magnesium sulfate and the chromium salts were washed 3× with acetone. The solvent was removed in vacuo to give a solid which was triturated with ethanol. The resulting crystals were isolated by filtration and rinsed 3× with diethyl ether. After drying, 5.0 g of product was obtained. H' NMR CDCl3 4.0 (singlet, 2H) 3.3 (triplet, 2H) 2.6 (triplet, 2H) 2.3 (multiplet, 2H).

후처리

  1. temperatureto maintain a brown color for at least 10 minutes without need for additional reagent
  2. filtrationThe mixture was filtered through anhydrous magnesium sulfate
  3. washthe chromium salts were washed 3× with acetone
  4. customThe solvent was removed in vacuo
  5. customto give a solid which
  6. customwas triturated with ethanol
  7. customThe resulting crystals were isolated by filtration
  8. washrinsed 3× with diethyl ether
  9. customAfter drying

출처 및 근거

ORD 기록
ord-753f7b58542840c384b0fe9ee4159068
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845225

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