4-Toluenesulfonyl chloride → HCID 53748711, compound

HRID 1730873Notes

Reaction equation

HRID 1730873 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:21])[CH2:13][CH2:14][CH:15]=[CH:16][C:17]#[C:18][CH2:19][CH3:20]>N1C=CC=CC=1>[S:7]([O:21][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][C:17]#[C:18][CH2:19][CH3:20])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 71373320Non-4-en-6-yn-1-ol

Product 1

HCID 53748711HCID 53748711, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of p-toluenesulfonyl chloride (22.4 g., 0.12 moles) and 50 ml. of anhydrous pyridine is added 14 g. of non-4-en-6-yn-1-ol (0.107 moles) with ice bath cooling. The mixture is stirred for 1 hour and then is stored at 0° overnight. Ice is added to the mixture which is extracted with several portions of 50:50 ether/hexane. The combined organic phase is washed with 5% HCl, water, saturated sodium bicarbonate and dried over sodium sulfate. Removal of solvent at reduced pressure and subsequent solvent removal at 0.1 mm. for 1 hour gives 1-tosyloxy-non-4-en-6yne (28 g.).

Workup

  1. waitis stored at 0° overnight
  2. additionIce is added to the mixture which
  3. extractionis extracted with several portions of 50:50 ether/hexane
  4. washThe combined organic phase is washed with 5% HCl, water, saturated sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. customRemoval of solvent
  7. customat reduced pressure and subsequent solvent removal at 0.1 mm

Sources & evidence

ORD record
ord-50fb8b268da14f11838019e345d86592
Source dataset
uspto-grants-1976_11
Patent number
US03994896

Reaction notes

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