Water → HCID 10585588, compound

HRID 376385Notes

Reaction equation

HRID 376385 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5](=[O:16])[C:6]2[C:12]([OH:13])=[CH:11][C:10]([O:14][CH3:15])=[CH:9][C:7]=2[CH:8]=1.[C-:17]#[N:18].[Na+].O>CS(C)=O>[C:17]([CH2:2][C:3]1[O:4][C:5](=[O:16])[C:6]2[C:12]([OH:13])=[CH:11][C:10]([O:14][CH3:15])=[CH:9][C:7]=2[CH:8]=1)#[N:18]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 10657711HCID 10657711, compound

Product 1

HCID 10585588HCID 10585588, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
15 °C

Procedure

5.00 g (20.78 mmol) of the 3-chloromethyl-8-hydroxy-6-methoxy-1-oxo-1H-2-benzopyran obtained in Example 2 was dissolved in 70 ml of dimethyl sulfoxide. 4.29 g (83.11 mmol) of sodium cyanide was added thereto, and the resulting mixture was stirred under an atmosphere of nitrogen at 15° C. for 30 minutes. After the addition of 300 ml of water, the reaction mixture was extracted with 600 ml and 250 ml×3 portions of ethyl acetate. The organic layer was washed three times with 200 ml portions of a 20% aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated to about 300 ml under reduced pressure. After the addition of 3 g of activated carbon, this solution was heated under reflux for 10 minutes. The activated carbon was removed by filtration through Celite, and the filtrate and the washings were concentrated to about 100 ml. The precipitated crystals were dissolved by heating under reflux, and then cooled with ice. The reprecipitated crystals were filtered off to obtain 4.08 g of the title compound in an 84% yield.

Workup

  1. extractionthe reaction mixture was extracted with 600 ml and 250 ml×3 portions of ethyl acetate
  2. washThe organic layer was washed three times with 200 ml portions of a 20% aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to about 300 ml under reduced pressure
  5. additionAfter the addition of 3 g of activated carbon
  6. temperaturethis solution was heated
  7. temperatureunder reflux for 10 minutes
  8. customThe activated carbon was removed by filtration through Celite
  9. concentrationthe filtrate and the washings were concentrated to about 100 ml
  10. dissolutionThe precipitated crystals were dissolved
  11. temperatureby heating
  12. temperatureunder reflux
  13. temperaturecooled with ice
  14. filtrationThe reprecipitated crystals were filtered off

Sources & evidence

ORD record
ord-401e08abfa944d3ba51229e4fd4189a3
Source dataset
uspto-grants-2000_02
Patent number
US06020363

Reaction notes

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