Triethylamine → Methanesulfonic acid 2-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]ethyl ester

HRID 1528817Notes

Reaction equation

HRID 1528817 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][CH2:15][OH:16])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][CH2:15][O:16][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 665772962-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-ethanol

Product 1

HCID 86652398Methanesulfonic acid 2-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-ethanol (0.100 g, 0.35 mmol) and triethylamine (0.10 mL, 0.71 mmol) in THF at 0° C. was added methanesulfonyl chloride (0.05 mL, 0.62 mmol) and the reaction stirred at 0° C. for 1 hour. The mixture was diluted with H2O and extracted with EtOAc, and the combined organic layers were washed with H2O, saturated aqueous NaHCO3, and brine. Dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washthe combined organic layers were washed with H2O, saturated aqueous NaHCO3, and brine
  3. dry with materialDried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5c39356cec564f52b837d4a41558e85b
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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