Hydrochloric Acid → HCID 19092508, compound

HRID 487635Notes

Reaction equation

HRID 487635 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][CH:14]=[C:13]([CH2:17][O:18][Si](C(C)(C)C)(C)C)[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]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[C:12]3=[O:26])[C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 21746911HCID 21746911, compound

Product 1

HCID 19092508HCID 19092508, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

In 9.00 ml of methanol, is dissolved 877 mg of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-3-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzz[b]pyran obtained in Example 17. Then, 2.20 ml of 4N hydrochloric acid in dioxane is added to the solution at 0° C. and reacted at room temperature for one hour. 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 and further by silica gel column chromatography using 1/1 mixture of ethyl acetate/n-hexane as a developing solvent. Thus, 472 mg of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-3-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran is obtained.

Workup

  1. customreacted at room temperature for one hour
  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
  11. addition1/1 mixture of ethyl acetate/n-hexane as a developing solvent

Sources & evidence

ORD record
ord-3f616e3da1f245dead590b48e2414edb
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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