3-Butyn-1-OL → But-3-yn-1-yl methanesulfonate

HRID 2175917Notes

Reaction equation

HRID 2175917 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[CH3:6][S:7](Cl)(=[O:9])=[O:8]>C(Cl)Cl>[CH3:6][S:7]([O:5][CH2:1][CH2:2][C:3]#[CH:4])(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 135663-Butyn-1-OLHCID 31297Methanesulfonyl chloride

Product 1

HCID 11378578But-3-yn-1-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of but-3-yn-1-ol (45.0 g, 0.64 mol) and methanesulfonyl chloride (81.0 g, 0.71 mol) in 600 mL of DCM was added TEA (78.0 g, 0.77 mol) dropwise at 0° C. The resulting mixture was stirred at room temperature for 2 hours then concentrated to dryness. The residue was dissolved in 1 L of EtOAc then washed with 1N HCl (2×200 mL), brine (200 mL), dried over anhydrous Na2SO4 and concentrated to afford but-3-yn-1-yl methanesulfonate.

Workup

  1. concentrationthen concentrated to dryness
  2. dissolutionThe residue was dissolved in 1 L of EtOAc
  3. washthen washed with 1N HCl (2×200 mL), brine (200 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3bfb4439340c4b91b97ed62fe1791823
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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