Triethylamine → 2-Azidoethyl methanesulfonate

HRID 539529Notes

Reaction equation

HRID 539529 reaction equation
[N:1]([CH2:4][CH2:5][OH:6])=[N+:2]=[N-:3].C(N(CC)CC)C.[S:14](Cl)([CH3:17])(=[O:16])=[O:15].C(=O)(O)[O-].[Na+]>C1COCC1.C(Cl)Cl>[CH3:17][S:14]([O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])(=[O:16])=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1231182-AzidoethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 112751972-Azidoethyl methanesulfonateYield 89.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 2-azidoethanol (1.00 g, 11.49 mmol) in THF (25 mL) and triethylamine (Et3N) (2.418 mL, 17.24 mmol) was added mesyl chloride (1.328 mL, 17.24 mmol) at 0° C., and the mixture was allowed to warm to room temperature. Stirring continued for 3 h, during which TLC revealed a quantitative conversion into a higher Rf product. CH2Cl2 (70 mL) and saturated sodium bicarbonate (50 mL) were added, and the two layers were separated. The organic layer was washed with sodium bicarbonate (2×50 mL), saturated brine (45 mL) and dried over Na2SO4. Solvent was evaporated off to give crude compound 156a (1.70 g) as a colorless oil, which was used for next step without further purification.

Workup

  1. customthe two layers were separated
  2. washThe organic layer was washed with sodium bicarbonate (2×50 mL), saturated brine (45 mL)
  3. dry with materialdried over Na2SO4
  4. customSolvent was evaporated off

Sources & evidence

ORD record
ord-2c1b147373ce449dbce4d4165c63cbf4
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

Loading…