Methanesulfonyl chloride → Methanesulfonic acid 5-furan-2-yl-isoxazol-3-ylmethyl ester

HRID 606284Notes

Reaction equation

HRID 606284 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8]([CH2:11][OH:12])[CH:7]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8]([CH2:11][O:12][S:14]([CH3:13])(=[O:16])=[O:15])[CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 7164591(5-(Furan-2-yl)-1,2-oxazol-3-yl)methanol

Product 1

HCID 57696260Methanesulfonic acid 5-furan-2-yl-isoxazol-3-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.41 g of (5-furan-2-yl-isoxazol-3-yl)-methanol and 1.77 mL of TEA in 45 mL of methylene chloride was slowly added 0.73 mL of methanesulfonyl chloride at 0° C. After stirring for 1 hr, the reaction solution was washed with water and 1N HCl, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to provide 10.0 g of methanesulfonic acid 5-furan-2-yl-isoxazol-3-ylmethyl ester. This concentrate was used for the next step without further purification.

Workup

  1. customat 0° C
  2. washthe reaction solution was washed with water and 1N HCl
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f73d0086440425a8bf7abe2249dd202
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

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