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

HRID 345892Notes

Reaction equation

HRID 345892 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f486780a4f764b2fbb80c74641faa0a5
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

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