Triethylamine → But-3-yn-1-yl methanesulfonate

HRID 1984079Notes

Reaction equation

HRID 1984079 reaction equation
[CH:1]#[C:2][CH:3]([OH:5])C.CCN(CC)CC.[CH3:13][S:14](Cl)(=[O:16])=[O:15].[C:18]([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH2:3]([O:5][S:14]([CH3:13])(=[O:16])=[O:15])[CH2:2][C:1]#[CH:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-but-1-ynol (5.62 g, 80.2 mmoL) and Et3N (14.5 mL, 104 mmol) in DCM (40 mL) was treated with MsCl (7.48 mL, 96.2 mmol) at 0° C. for 10 min. Work-up (water; sat. aq. NaHCO3), drying (Na2SO4), and concetration gave the title compound as a pale orange oil. 1H NMR (CDCl3) δ 4.32 (t, 2H), 3.07 (s, 3H), 2.67 (td, 2H), 2.09 (t, 2H).

Workup

  1. dry with materialdrying (Na2SO4), and concetration

Sources & evidence

ORD record
ord-2d55f9c3397f49dcaac02b15622fe13f
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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