4-Toluenesulfonyl chloride → 3-Tosyloxy-5-hexyn-2-one

HRID 2231193Notes

Reaction equation

HRID 2231193 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH:12][CH:13]([CH2:17][C:18]#[CH:19])[C:14](=[O:16])[CH3:15].C(N(CC)CC)C>C(Cl)Cl>[S:1]([O:12][CH:13]([CH2:17][C:18]#[CH:19])[C:14](=[O:16])[CH3:15])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 212863473-Hydroxy-5-hexyn-2-one

Product 1

HCID 138258933-Tosyloxy-5-hexyn-2-oneYield 55.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tosyl chloride (3.81 g) was added to a solution of 3-hydroxy-5-hexyn-2-one (2.24 g) and triethylamine (2.424 g) in methylene chloride (20 ml) under ice-cooling. After being stirred for 2.5 hours, the mixture was washed with water, dried over magnesium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (60 g) using methylene chloride as an eluent to give an oil of 3-tosyloxy-5-hexyn-2-one (2.94 g).

Workup

  1. temperaturecooling
  2. washthe mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe oily residue was purified by column chromatography on silica gel (60 g)

Sources & evidence

ORD record
ord-545074704a2243fa890c87d5ebe123c3
Source dataset
uspto-grants-1988_11
Patent number
US04782055

Reaction notes

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