Hydrochloric Acid → HCID 178467617, compound

HRID 465460Notes

Reaction equation

HRID 465460 reaction equation
C1[O:14][C:4]([CH3:13])([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)OC1.[Na].Cl[CH2:17][C:18]1[O:22][N:21](C2CCC=CO2)[C:20](=[O:29])[CH:19]=1.Cl>C(O)C.CC(C)=O>[CH2:5]([C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:17][C:18]2[O:22][N:21]=[C:20]([OH:29])[CH:19]=2)=[CH:10][CH:11]=1)[C:4]([CH3:13])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 198745685-chloromethyl-2-(1,2,3,4-tetrahydropyran-2-yl)isoxazol-3-(2H)oneHCID 566304374-Hydroxyphenylpropan-2-one ethylene ketal

Product 1

HCID 178467617HCID 178467617, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent3×

Procedure

A solution of (4-hydroxyphenyl)propan-2-one ethylene ketal (1.4 g) in ethanol, was treated with a solution of sodium (0.16 g) in ethanol (25 ml) and heated under reflux for 10 minutes. A solution of 5-chloromethyl-2-(1,2,3,4-tetrahydropyran-2-yl)isoxazol-3-(2H)one (1.5 g) in ethanol was added dropwise, and the reaction was heated for 18 hr. The cooled solution was evaporated in vacuo, the residue partitioned between ethylacetate and water, the organic layer separated, dried (magnesium sulphate), and the solvent removed in vacuo to give an oil which was chromatographed on silica. Elution with ether: 60:80 petrol (1:1) gave an oil which was dissolved in acetone and treated with 2M hydrochloric acid solution (5 ml) and allowed to stand at room temperature for 4 hr. The solvent was removed in vacuo, the residue dissolved in ethyl acetate, washed with 1.2M sodium bicarbonate solution (1×50 ml), dried (magnesium sulphate , filtered and evaporated to give 5-(4-acetonylphenoxymethyl)3-hydroxyisoxazole.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 10 minutes
  3. temperaturethe reaction was heated for 18 hr
  4. customThe cooled solution was evaporated in vacuo
  5. customthe residue partitioned between ethylacetate and water
  6. customthe organic layer separated
  7. dry with materialdried (magnesium sulphate)
  8. customthe solvent removed in vacuo
  9. customto give an oil which
  10. customwas chromatographed on silica
  11. washElution with ether
  12. custom60:80 petrol (1:1) gave an oil which
  13. customThe solvent was removed in vacuo
  14. dissolutionthe residue dissolved in ethyl acetate
  15. washwashed with 1.2M sodium bicarbonate solution (1×50 ml)
  16. dry with materialdried (magnesium sulphate
  17. filtrationfiltered
  18. customevaporated

Sources & evidence

ORD record
ord-97d05a56ed9042f7a96f4bb7db8cd34a
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

Loading…