Hydrochloric Acid → HCID 19092510, compound

HRID 487632Notes

Reaction equation

HRID 487632 reaction equation
[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[O:7][C:8]([CH3:28])([CH3:27])[CH:9]=[C:10]([N:11]3[CH:16]=[C:15]([CH2:17][O:18][Si](C(C)(C)C)(C)C)[CH:14]=[CH:13][C:12]3=[O:26])[C:5]=2[CH:4]=1)#[N:2].Cl.O>CO.O1CCOCC1>[C:1]([C:3]1[CH:30]=[CH:29][C:6]2[O:7][C:8]([CH3:27])([CH3:28])[CH:9]=[C:10]([N:11]3[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:12]3=[O:26])[C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 21746905HCID 21746905, compound

Product 1

HCID 19092510HCID 19092510, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

In 11.5 ml of methanol, is dissolved 1.16 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-5-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 13. Then, 2.87 ml of 4N hydrochloric acid in dioxane is added to the solution at 0° C., and reacted at room temperature for 1.5 hours. After stopping the reaction by adding water, the reaction mixture is extracted with ethyl acetate. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The inorganic matter is filtered off, and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by silica gel column chromatography using 1/20 mixture of methanol/methylene chloride as a developing solvent to obtain 0.80 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-5-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran.

Workup

  1. customreacted at room temperature for 1.5 hours
  2. customthe reaction
  3. extractionthe reaction mixture is extracted with ethyl acetate
  4. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe inorganic matter is filtered off
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue thus obtained
  9. customis purified by silica gel column chromatography
  10. addition1/20 mixture of methanol/methylene chloride as a developing solvent

Sources & evidence

ORD record
ord-8984899f5ec2479eabe06e4ce8583bbe
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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