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

HRID 488225Notes

Reaction equation

HRID 488225 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 degrees. After 20 minutes, the excess Jones reagent was destroyed with ethanol (ca 1 ml) and the mixture was diluated 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. customThe organic phase was separated
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated down
  5. customto give an oil, which
  6. customwas purified by preparative silica plates

Sources & evidence

ORD record
ord-ae999914e95a420e93055ae0f57f8deb
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Reaction notes

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