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

HRID 1109885Notes

Reaction equation

HRID 1109885 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 diluted with water. The organic phase was is 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 is 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-4c699fc345914e52817ce5d15d80a87c
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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