4-(5-Hydroxy-3-hexadecynyl)-2-triethylsilylfuran → 4-(5-Oxo-3-hexadecynyl)-2-triethylsilylfuran

HRID 1681516ノート

反応式

HRID 1681516 の反応式
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH:15]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:16]#[C:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])[O:23][CH:24]=1>S(=O)(=O)(O)O.CC(C)=O>[O:14]=[C:15]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:16]#[C:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])[O:23][CH:24]=1

参加物

5

反応物 2

HCID 150371064-(5-Hydroxy-3-hexadecynyl)-2-triethylsilylfuranHCID 131709961Jones' reagent

生成物 1

HCID 150371074-(5-Oxo-3-hexadecynyl)-2-triethylsilylfuran

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 1118Sulfuric Acid溶媒

実験手順

Jones reagent (a 2.6M solution in sulfuric acid; 0.13 ml, 0.36 mmol) was added dropwise to a solution of 4-(5-hydroxy-3-hexadecynyl)-2-triethylsilylfuran (136.4 mg, 0.33 mmol) in acetone (5 ml) at 0 degrees. After 20 minutes, the excess Jones reagent was destroyed with ethanol (ca 1 ml) and the mixture was diluted with water. The organic phase was separated, dried (magnesium sulfate) and evaporated down to give an oil, which was purified by preparative silica plates to give the titled ketone.

後処理

  1. customthe excess Jones reagent was destroyed with ethanol (ca 1 ml)
  2. additionthe mixture was diluted with water
  3. customThe organic phase was separated
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated down
  6. customto give an oil, which
  7. customwas purified by preparative silica plates

出典と根拠

ORDレコード
ord-4eb508bac72a47efbfac319d98972069
出典データセット
uspto-grants-1992_12
特許番号
US05171863

反応ノート

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