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

HRID 4288Notes

Reaction equation

HRID 4288 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-cd3f0cac90124ff0adb84e6417ad574b
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Reaction notes

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