Water → Methanesulfonic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester

HRID 72329Notes

Reaction equation

HRID 72329 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][OH:21])[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(N(CC)CC)C.O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][O:21][S:23]([CH3:22])(=[O:25])=[O:24])[O:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 64164588[3-(4-Benzyloxy-phenyl)-isoxazol-5-yl]-methanol

Product 1

HCID 59667381Methanesulfonic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methanol (3.0 g, 10.6 mmol) was dissolved in methylene chloride (50 ml, 0.2 M), to which solution were added dropwise MsCl (1.23 ml, 15.9 mmol) and triethylamine (2.23 ml, 16 mmol-), and a reaction was performed at room temperature for 4 hours. The completion of the reaction was confirmed by liquid chromatography, 5 ml of water was added to the mixture, and the resulting solution was extracted with water and methylene chloride. The organic solvent layer was distilled under reduced pressure to obtain a crude solid compound. This was recrystallized from hexane:ethyl acetate (5:1) to obtain methanesulfonic acid 3-(4-benzyloxy-phenyl)-isoxazol-5-ylmethyl ester as a white solid compound.

Workup

  1. additionwas added to the mixture
  2. extractionthe resulting solution was extracted with water and methylene chloride
  3. distillationThe organic solvent layer was distilled under reduced pressure
  4. customto obtain a crude solid compound
  5. customThis was recrystallized from hexane:ethyl acetate (5:1)

Sources & evidence

ORD record
ord-10ccffeaddfe447c99849f2d3808a407
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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