Sulfuric Acid → 3-Mesyloxy-5-hexyn-2-one

HRID 4290Notes

Reaction equation

HRID 4290 reaction equation
[S:1]([O:5][CH:6]([CH2:11][C:12]#[CH:13])[C:7]([O:9]C)=[CH2:8])([CH3:4])(=[O:3])=[O:2].S(=O)(=O)(O)O>CC(C)=O>[S:1]([O:5][CH:6]([CH2:11][C:12]#[CH:13])[C:7](=[O:9])[CH3:8])([CH3:4])(=[O:2])=[O:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 201523303-Mesyloxy-2-methoxy-1-hexen-5-yne

Product 1

HCID 143683463-Mesyloxy-5-hexyn-2-oneYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-mesyloxy-2-methoxy-1-hexen-5-yne (0.5 g) in acetone (1.5 ml) was added 20% sulfuric acid (1.5 ml) under ice-cooling and the mixture was stirred for 1.5 hours under the same conditions and then for 1.5 hours at room temperature. Acetone was evaporated in vacuo and the residue was extracted with methylene chloride. The extract was washed successively with water, aqueous sodium bicarbonate solution, and brine, dried over magnesium sulfate, and evaporated in vacuo to give 3-mesyloxy-5-hexyn-2-one (0.41 g).

Workup

  1. temperaturecooling
  2. waitfor 1.5 hours at room temperature
  3. customAcetone was evaporated in vacuo
  4. extractionthe residue was extracted with methylene chloride
  5. washThe extract was washed successively with water, aqueous sodium bicarbonate solution, and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-b8f160543fa44baea176707de4dac95e
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Reaction notes

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