Sulfuric Acid → HCID 57847035, compound

HRID 1009925Notes

Reaction equation

HRID 1009925 reaction equation
C([O:3][C:4](=[O:13])[CH2:5][C:6]1(O)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)C.[C:14](#[N:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.S(=O)(=O)(O)[OH:23]>O>[C:14]([NH:21][C:6]1([CH2:5][C:4]([OH:3])=[O:13])[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1)(=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7505BenzonitrileHCID 21936035Ethyl tetrahydro-4-hydroxy-2H-pyran-4-acetate

Product 1

HCID 57847035HCID 57847035, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl(4-hydroxytetrahydro-2H-pyran-4-yl)acetate (6.73 g, 35.8 mmol) and benzonitrile (4.05 ml, 39.3 mmol) was added conc. sulfuric acid (25 ml) under ice-cooling. After stirring at room temperature for 16 hrs., the reaction mixture was added to water (100 ml) under ice-cooling, and the mixture was extracted with ethyl acetate. The extract washed with saturated aqueous sodium hydrogen carbonate solution, then with saturated brine and dried over anhydrous MgSO4. After concentration under reduced pressure, ethanol (50 ml) and 50% aqueous potassium hydroxide solution (10 ml) was added to the obtained residue, and the mixture was heated under reflux for 6 hrs. Water (200 ml) was added to the reaction mixture and the mixture was washed with diethyl ether. The aqueous layer was acidified (pH 2) with 5N hydrochloric acid, extracted with ethyl acetate-tetrahydrofuran (2:1, v/v). The extract was washed with saturated brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The obtained solid was collected by filtration and washed with diisopropyl ether to give the title compound (1.64 g, 17%) as colorless crystals.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract washed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialwith saturated brine and dried over anhydrous MgSO4
  6. concentrationAfter concentration under reduced pressure, ethanol (50 ml) and 50% aqueous potassium hydroxide solution (10 ml)
  7. additionwas added to the obtained residue
  8. temperaturethe mixture was heated
  9. temperatureunder reflux for 6 hrs
  10. additionWater (200 ml) was added to the reaction mixture
  11. washthe mixture was washed with diethyl ether
  12. extractionextracted with ethyl acetate-tetrahydrofuran (2:1
  13. washThe extract was washed with saturated brine
  14. dry with materialdried over anhydrous Na2SO4
  15. concentrationconcentrated under reduced pressure
  16. filtrationThe obtained solid was collected by filtration
  17. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-8c320cdedddb44a18dd3d862cbc92fd7
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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