Diethyl Ether → HCID 131714596, compound

HRID 1380338Notes

Reaction equation

HRID 1380338 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C([O:26]CC)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][CH2:10][CH2:11][OH:12])=[CH:6][CH:7]=1.[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O-:26])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 122603533-Butyn-1-ol, 4-(4-chlorophenyl)-

Product 1

HCID 131714596HCID 131714596, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 13.3 g (0.0736 mole) of 4-(4-chlorophenyl)-3-butyn-1-ol in 70 ml pyridine and cool to 0° C. Add 16 g (0.0837 mole) of p-toluenesulfonyl chloride and stir in ice bath for one hour. Store in freezer over night. Add 200 ml diethyl ether and then wash with 3×150 ml 1N hydrochloric acid. The organic layer is then washed with 50 ml saturated aqueous sodium bicarbonate solution and then dried over magnesium sulfate. Evaporate solvent to obtain the title compound.

Workup

  1. waitStore in freezer over night
  2. washwash with 3×150 ml 1N hydrochloric acid
  3. washThe organic layer is then washed with 50 ml saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-ad500242860a43f884504abb15f382f6
Source dataset
uspto-grants-1986_04
Patent number
US04581370

Reaction notes

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