Triethylamine → Methanesulfonic acid 1-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-ethyl ester

HRID 273135Notes

Reaction equation

HRID 273135 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]([OH:15])[CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]([O:15][S:24]([CH3:23])(=[O:26])=[O:25])[CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57528604HCID 57528604, compound

Product 1

HCID 58812362Methanesulfonic acid 1-[5-(3-Chloro-phenyl)-isoxazol-3-yl]-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a screw cap vial equipped with stir bar was added 1-[5-(3-chloro-phenyl)-isoxazol-3-yl]-ethanol (110 mg, 0.49 mmol), dichloromethane (3 ml) and triethylamine (0.34 ml, 2.46 mmol). Cooled the mixture down to 0° C. and to it added methane sulfonyl chloride (0.08 ml, 0.98 mmol). Left the reaction mixture stirring at room temperature for 30 min. Reaction was quenched with saturated sodium bicarbonate (aqueous, 40 ml) and extracted with dichloromethane (3×30 ml). Combined organic phase was washed with brine (40 ml), dried (sodium sulfate), filtered and concentrated, in-vacuo to isolate the desired compound as brown oil.

Workup

  1. customIn a screw cap vial
  2. customequipped
  3. waitLeft the reaction mixture
  4. stirringstirring at room temperature for 30 min
  5. customReaction
  6. customwas quenched with saturated sodium bicarbonate (aqueous, 40 ml)
  7. extractionextracted with dichloromethane (3×30 ml)
  8. washCombined organic phase was washed with brine (40 ml)
  9. dry with materialdried (sodium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-6bf20a55beb241c79821c8b2e059208d
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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