Phosphate → HCID 19092538, compound

HRID 487641Notes

Reaction equation

HRID 487641 reaction equation
[C:1]([C:3]1[CH:28]=[CH:27][C:6]2[O:7][C:8]([CH3:26])([CH3:25])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH:17](O)[CH2:18][Si](C)(C)C)=[CH:13][C:12]3=[O:24])[C:5]=2[CH:4]=1)#[N:2].[H-].[Na+].P([O-])([O-])([O-])=O>O1CCCC1>[C:1]([C:3]1[CH:28]=[CH:27][C:6]2[O:7][C:8]([CH3:25])([CH3:26])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH:17]=[CH2:18])=[CH:13][C:12]3=[O:24])[C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 19092583HCID 19092583, compound

Product 1

HCID 19092538HCID 19092538, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 22 ml of anhydrous tetrahydrofuran, is dissolved 875 mg of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy-2-trimethylsilylethyl)-1-pyridinyl}-2H-benzo[b]pyran obtained in Example 26. Then, 89 mg of 60% oily sodium hydride is added to the solution at room temperature and reacted at room temperature for 4 hours. After stopping the reaction by adding 0.2 M phosphate buffer, the reaction mixture is extracted with ethyl acetate. The organic layer is washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. Then, 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 1/10 mixture of ethyl acetate/methylene chloride as a developing solvent. Thus, 493 mg of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-vinyl-1-pyridinyl)-2H-benzo[b]pyran is obtained.

Workup

  1. customreacted at room temperature for 4 hours
  2. customthe reaction
  3. extractionthe reaction mixture is extracted with ethyl acetate
  4. washThe organic layer is washed successively with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThen, the 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. addition1/10 mixture of ethyl acetate/methylene chloride as a developing solvent

Sources & evidence

ORD record
ord-bbd2cb61a2e44a459dee8c3934d405fc
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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