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

HRID 867937ノート

反応式

HRID 867937 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d266dfb256b7486bb2b480c2d3beb8b1
出典データセット
uspto-grants-1988_10
特許番号
US04777167

反応ノート

読み込み中…