HCID 19991618, compound → HCID 19991598, compound

HRID 345900Notes

Reaction equation

HRID 345900 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH:15]([C:30]#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:16][CH2:17][C:18]1[CH:19]=[C:20]([Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[O:21][CH:22]=1>S(=O)(=O)(O)O.CC(C)=O>[O:14]=[C:15]([C:30]#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:16][CH2:17][C:18]1[CH:19]=[C:20]([Si:23]([CH2:26][CH3:27])([CH2:24][CH3:25])[CH2:28][CH3:29])[O:21][CH:22]=1

Participants

5

Reactant 2

HCID 19991618HCID 19991618, compoundHCID 131709961Jones' reagent

Product 1

HCID 19991598HCID 19991598, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolvent

Procedure

Jones reagent (a 2.67M solution in sulfuric acid; 50 μl, 0.14 mmol) was added to a solution of 4-(3-hydroxy-4-hexadecynyl)-2-triethylsilylfuran (53.6 mg, 0.13 mmol) in acetone (5 ml) at 0°. After 25 minutes, the mixture was quenched with ethanol, diluted with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by preparative silica plates to give the titled ketone.

Workup

  1. customthe mixture was quenched with ethanol
  2. additiondiluted with water
  3. extractionwas extracted with ethyl ether
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil, which
  7. customwas purified by preparative silica plates

Sources & evidence

ORD record
ord-460904ef31344bc9b96b66d4d0b0d572
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

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