Water → HCID 58489054, compound

HRID 909399Notes

Reaction equation

HRID 909399 reaction equation
[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7]([OH:10])=[N:8][O:9][C:5]=2[CH:4]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:30]1[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31]1.O>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[N:8]([CH:31]3[CH2:32][CH2:33][CH2:34][CH2:35][O:30]3)[O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 22033616Pyridinium.p-toluenesulfonateHCID 178518985HCID 178518985, compound

Product 1

HCID 58489054HCID 58489054, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 75 mL of methylene chloride, 5.00 g of 6-(chloromethyl)-1,2-benzisoxazol-3-ol was suspended, and to this was added 0.137 g of pyridinium p-toluenesulfonic acid and 2.98 mL of 3,4-dihydro-2H-pyran. This was stirred for 8 hours at room temperature. To the reaction mixture was added 30 mL of water and an organic layer was separated. An aqueous layer was extracted with 10 mL of methylene chloride, and this along with the organic layer was washed with an aqueous saturated sodium chloride solution and dried with anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and 20 mL of diisopropyl ether was added to the obtained residue. A seed crystal was added and, after 30 minutes of stirring at room temperature, solids were filtered to obtain 6.65 g of 6-(chloromethyl)-2-(tetrahydro-2H-pyran-2-yl)-1,2-benzisoxazol-3(2H)-one in the form of a pale yellowish-white solid.

Workup

  1. customan organic layer was separated
  2. extractionAn aqueous layer was extracted with 10 mL of methylene chloride
  3. washthis along with the organic layer was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationSolvent was distilled off under reduced pressure, and 20 mL of diisopropyl ether
  6. additionwas added to the obtained residue
  7. additionA seed crystal was added and, after 30 minutes
  8. stirringof stirring at room temperature
  9. filtrationsolids were filtered

Sources & evidence

ORD record
ord-1c4f6ac434734dbcacddc1e0695fd150
Source dataset
uspto-grants-2011_09
Patent number
US08017789B2

Reaction notes

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