Methanesulfonyl chloride → HCID 18408512, compound

HRID 993025Notes

Reaction equation

HRID 993025 reaction equation
O[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)[O:5][N:4]=1.[Cl-].[Li+].CS([Cl:26])(=O)=O>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:26][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)[O:5][N:4]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 18408515HCID 18408515, compound

Product 1

HCID 18408512HCID 18408512, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Hydroxymethyl-5-(3,4,5-trimethoxyphenyl)isoxazole (1.62 g) was dissolved in pyridine (10 mL), and lithium chloride (336 mg) was added to the solution. Methanesulfonyl chloride (908 mg) was added dropwise to the resultant mixture under ice cooling, and the mixture was stirred at room temperature for2 hours. The reaction mixture was diluted with ethyl acetate, washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to obtain the title compound.

Workup

  1. washwashed with 2 M hydrochloric acid, water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ed8f0204d487412d8eb04e09787f513e
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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