4-Toluenesulfonyl chloride → HCID 11128411, compound

HRID 2212326Notes

Reaction equation

HRID 2212326 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:13])[C:9]#[C:10][CH2:11][OH:12].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>O1CCOCC1>[OH:12][CH2:11][C:10]#[C:9][CH2:8][O:13][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 80662-Butyne-1,4-diolHCID 8471Triethylamine

Product 1

HCID 11128411HCID 11128411, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

At 10° C., a solution of triethylamine (17.5 ml, 128.0 mmol) in absolute dioxane (60 ml) is added dropwise to a solution of but-2-yne-1,4-diol (10 g, 116.1 mmol) and 4-toluenesulfonyl chloride (24.4 g, 128.0 mmol) in absolute dioxane (230 ml), and the mixture is stirred for 2 h. The mixture is then stirred at RT overnight. The reaction mixture is filtered off with suction through kieselguhr, and the filter cake is washed with ethyl acetate (20 ml). The organic phase is concentrated under reduced pressure. Further purification is carried out by chromatography [toluene/acetone (8.5:1.5)] on a silica gel column. This gives the title compound (7.5 g) as a light yellow oil. TLC, silica gel (glass plates), [toluene/acetone (8:2)], Rf=0.49.

Workup

  1. stirringThe mixture is then stirred at RT overnight
  2. filtrationThe reaction mixture is filtered off with suction through kieselguhr
  3. washthe filter cake is washed with ethyl acetate (20 ml)
  4. concentrationThe organic phase is concentrated under reduced pressure
  5. customFurther purification

Sources & evidence

ORD record
ord-1b7c1e9cd5524f12aa5b99859b5e6fcd
Source dataset
uspto-grants-2006_09
Patent number
US07101911B2

Reaction notes

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