Triethylamine → [5-(3-Chlorophenyl)isoxazol-3-yl]methyl methanesulfonate

HRID 2102306Notes

Reaction equation

HRID 2102306 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[O:24][N:23]=[C:22]([CH2:25][OH:26])[CH:21]=2)[CH:17]=[CH:18][CH:19]=1>ClCCl>[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[O:24][N:23]=[C:22]([CH2:25][O:26][S:9]([CH3:8])(=[O:11])=[O:10])[CH:21]=2)[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanol

Product 1

HCID 57838012[5-(3-Chlorophenyl)isoxazol-3-yl]methyl methanesulfonateYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyl amine (965 mg, 9.5 mmol) and methanesulfonyl chloride (820 mg, 7.2 mmol) were added to a solution of [5-(3-chloro-phenyl)-isoxazol-3-yl]-methanol (1.0 g, 4.8 mmol) in dichloromethane (50 mL) at 0° C. After 1 hour, the reaction mixture was quenched with cold saturated sodium bicarbonate and then the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford methanesulfonic acid 5-(3-chloro-phenyl)-isoxazol-3-ylmethyl ester (1.4 g, 100%, light brown solid). 1H NMR (CDCl3) δ (ppm): 7.80 (s, 1H), 7.70 (m, 1H), 7.45 (m, 2H), 6.73 (s, 1H), 5.37 (s, 2H), 3.16 (s, 3H).

Workup

  1. customthe reaction mixture was quenched with cold saturated sodium bicarbonate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e708443af2304e45a4e7c6f3d30204b6
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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