Methanesulfonyl chloride → 2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate

HRID 643990Notes

Reaction equation

HRID 643990 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:18][CH2:19][OH:20]>C(Cl)Cl>[CH3:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:18][CH2:19][O:20][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 105407732-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (4.98 g, 49.2 mmol) and methanesulfonyl chloride (3.38 g, 29.5 mmol) is added to a solution of 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethanol (5 g, 24.6 mmol) in 100 mL of DCM at 0° C. The resulting mixture is stirred at RT overnight. The mixture is then washed with water and brine, and the organic solution is dried over anhydrous magnesium sulfate and concentrated to give methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester as a yellow solid.

Workup

  1. washThe mixture is then washed with water and brine
  2. dry with materialthe organic solution is dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-847fce4be0644f2ab26361f5785b8909
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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