4-Toluenesulfonyl chloride → Pent-2-yn-1-yl 4-methylbenzene-1-sulfonate

HRID 1470692Notes

Reaction equation

HRID 1470692 reaction equation
[CH2:1]([OH:6])[C:2]#[C:3][CH2:4][CH3:5].[S:7](Cl)([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[OH-].[K+]>C1COCC1>[CH3:14][C:13]1[CH:15]=[CH:16][C:10]([S:7]([O:6][CH2:1][C:2]#[C:3][CH2:4][CH3:5])(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 804212-Pentyn-1-ol

Product 1

HCID 11770515Pent-2-yn-1-yl 4-methylbenzene-1-sulfonateYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-Pentyn-1-ol (60 g, 0.71 mol) in THF (420 mL) cooled to −5° C., tosyl chloride (142.9 g, 0.75 mol) and KOH (79.9 g, 1.42 mol) were added and the reaction mixture was stirred at room temperature for 1 h. After completion of starting material, the reaction mixture was extracted with ethyl acetate (300 mL×2), washed with water (100 mL×2), brine (50 mL×2) and dried over Na2SO4. The combined organic extracts were evaporated under reduced pressure to obtain the crude product which was purified by column chromatography (100-200 mesh silica gel, 20% EtOAc-hexane) to furnish pent-2-ynyl 4-methylbenzenesulfonate (110 g, 64%) as a light red liquid.

Workup

  1. extractionAfter completion of starting material, the reaction mixture was extracted with ethyl acetate (300 mL×2)
  2. washwashed with water (100 mL×2), brine (50 mL×2)
  3. dry with materialdried over Na2SO4
  4. customThe combined organic extracts were evaporated under reduced pressure
  5. customto obtain the crude product which
  6. customwas purified by column chromatography (100-200 mesh silica gel, 20% EtOAc-hexane)

Sources & evidence

ORD record
ord-84936afa232c40c395aca3f841fd4745
Source dataset
uspto-grants-2015_04
Patent number
US09006472B2

Reaction notes

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