Water → HCID 57736318, compound

HRID 2261336Notes

Reaction equation

HRID 2261336 reaction equation
[CH:1]([C:4]1[O:8][N:7]=[C:6]([CH:9](O)[CH3:10])[CH:5]=1)([CH3:3])[CH3:2].C1(C)C=CC(S([Cl:21])(=O)=O)=CC=1.O>N1C=CC=CC=1>[Cl:21][CH:9]([C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[O:8][N:7]=1)[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 45117986HCID 45117986, compound

Product 1

HCID 57736318HCID 57736318, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.66 g of 1-(5-i-propyl-isoxazol-3-yl)ethanol was dissolved in 30 ml of pyridine, and 7.20 g of 4-toluenesulfonyl chloride was then added under ice-cooling. The mixture was stirred for 5 hours under ice-cooling. After water was added, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 3.63 g of 3-(1-chloroethyl)-5-i-propylisoxazole.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d4e7d3d06434a2cbc6ff228710bcc87
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

Loading…