Triethylamine → Butyl (methylsulfonyloxy)acetate

HRID 1940260Notes

Reaction equation

HRID 1940260 reaction equation
[OH:1][CH2:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4].C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:1][CH2:2][C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 81882Butyl Glycolate

Product 1

HCID 21466675Butyl (methylsulfonyloxy)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

27.8 g (0.2 mol) of n-butyl hydroxyacetate (95% pure by GC) and 20.2 g (0.2 mol) of triethylamine are first introduced into 300 ml of dichloromethane at -5° C. 34.4 g (0.3 mol) of methanesulfonyl chloride in 50 ml of dichloromethane are slowly added dropwise at 0° to 5° C. Stirring of the batch at 0° C. is continued overnight, ice water is added, the phases are separated, and the aqueous phase is extracted twice with dichloromethane. The combined organic phases are dried, and the solvent is removed on a rotary evaporator leaving a colorless oil which is subjected to incipient distillation in vacuo. n-Butyl methylsulfonyloxyacetate is isolated as an almost colorless oil (40.5 g, 96.3% of theory, GC content 91%).

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted twice with dichloromethane
  3. customThe combined organic phases are dried
  4. customthe solvent is removed on a rotary evaporator
  5. customleaving a colorless oil which
  6. distillationis subjected to incipient distillation in vacuo

Sources & evidence

ORD record
ord-c616637380c94be2ad42b3372827df69
Source dataset
uspto-grants-1997_12
Patent number
US05698735

Reaction notes

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