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

HRID 345892노트

반응식

HRID 345892 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 1118Sulfuric Acid용매

실험 절차

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°. 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.

후처리

  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

출처 및 근거

ORD 기록
ord-f486780a4f764b2fbb80c74641faa0a5
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05059611

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