Hydrochloric Acid → 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran

HRID 487630Notes

Reaction equation

HRID 487630 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]=[CH:15][C:14]([CH2:17][O:18][Si](C(C)(C)C)(C)C)=[CH:13][C:12]3=[O:26])[C:5]=2[CH:4]=1)#[N:2].Cl>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]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:12]3=[O:26])[C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 217469076-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran

Product 1

HCID 190925956-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyranYield 100.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

In 10.5 ml of methanol, is dissolved 1.04 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 8. Then, 2.59 ml of a 4N hydrochloric acid in dioxane is added to the solution at 0° C., and the resulting mixture is reacted at room temperature for 2 hours. The reaction mixture is concentrated under reduced pressure, the residue is mixed with ethyl acetate and water and the product is extracted into the ethyl acetate. The organic layer is washed with saturated aqueou 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 is purified by silica gel column chromatography using 1/20 mixture of methanol/methylene chloride as a developing solvent to obtain 0.76 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran.

Workup

  1. customthe resulting mixture is reacted at room temperature for 2 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionthe residue is mixed with ethyl acetate and water
  4. extractionthe product is extracted into the ethyl acetate
  5. washThe organic layer is washed with saturated aqueou solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe inorganic matter is filtered off
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography
  10. addition1/20 mixture of methanol/methylene chloride as a developing solvent

Sources & evidence

ORD record
ord-50fefa3699dd49d299f4567d1e2a52ad
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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