Hydrochloric Acid → 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-(3-hydroxypropyl)-1-pyridinyl}-2H-benzo[b]pyran

HRID 487651Notes

Reaction equation

HRID 487651 reaction equation
[C:1]([C:3]1[CH:32]=[CH:31][C:6]2[O:7][C:8]([CH3:30])([CH3:29])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)=[CH:13][C:12]3=[O:28])[C:5]=2[CH:4]=1)#[N:2].Cl>CO.O1CCOCC1>[C:1]([C:3]1[CH:32]=[CH:31][C:6]2[O:7][C:8]([CH3:30])([CH3:29])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][OH:20])=[CH:13][C:12]3=[O:28])[C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 217469126-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(3-t-butyldimethylsilyloxypropyl)-1-pyridinyl}-2H-benzo[b]pyran

Product 1

HCID 190925556-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-(3-hydroxypropyl)-1-pyridinyl}-2H-benzo[b]pyranYield 94.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

In 7.50 ml of methanol, is dissolved 819 mg of 6-cyano-2,2-dimethyl-4-{2-oxo-4-(3-t-butyldimethylsilyloxypropyl)-1-pyridinyl}-2H-benzo[b]pyran obtained in Example 40. Then, 1.90 ml of 4N hydrochloric acid in dioxane is added thereto at 0° C., and reacted at room temperature for 30 minutes. The reaction mixture is concentrated under reduced pressure, the residue is mixed with ethyl acetate and water, and the product is extracted into 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 is purified by silica gel column chromatography using 1/10 mixture of methanol/methylene chloride as a developing solvent. Thus, 577 mg of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(3-hydroxypropyl)-1-pyridinyl}-2H-benzo[b]pyran is obtained.

Workup

  1. customat 0° C., and reacted at room temperature for 30 minutes
  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 ethyl acetate
  5. washThe organic layer is washed with saturated aqueous 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. addition1/10 mixture of methanol/methylene chloride as a developing solvent

Sources & evidence

ORD record
ord-d917f7d6683e45889506f8e8aab681ab
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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