tert-Butanol → 2-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

HRID 325177ノート

反応式

HRID 325177 の反応式
[OH:1][C:2]([CH3:14])([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8](SC)=[CH:7][CH:6]=1)=[O:4].O[O:16][S:17]([O-:19])=O.[K+].[C:21](O)(C)(C)C>C(Cl)Cl.O.CCOC(C)=O>[OH:1][C:2]([CH3:13])([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:17]([CH3:21])(=[O:19])=[O:16])=[CH:7][CH:6]=1)=[O:4]

参加物

7

反応物 3

HCID 6386tert-ButanolHCID 114131682-Hydroxy-4'(methylthio)isobutyrophenoneHCID 23707502Potassium hydroxy sulfite

生成物 1

HCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a cold (4° C.) solution of 2-hydroxy-2-methyl-1-(4-(methylthio)phenyl)-propan-1-one (45.0 g, 214 mmol, Step 2) in t-butanol (500 mL) and CH2Cl2 (500 mL) was added a solution of OXONE™ (194 g, 316 mmol) in water (1.4 L). The resulting suspension was stirred at r.t. for 18 h. The reaction was diluted with EtOAc (400 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2×250 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude product was dissolved in diethyl ether (250 mL), hexane was added (150 mL) and the product was swished for 2 h. The product was collected by filtration to give the title compound as a yellow solid.

後処理

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with EtOAc (2×250 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude product was dissolved in diethyl ether (250 mL)
  6. additionhexane was added (150 mL)
  7. waitthe product was swished for 2 h
  8. filtrationThe product was collected by filtration

出典と根拠

ORDレコード
ord-11d7fe5e9ef14bddbd21074f2be0ead1
出典データセット
uspto-grants-2001_04
特許番号
US06222048B1

反応ノート

読み込み中…