Sodium hydride → HCID 21746905, compound

HRID 487631Notes

Reaction equation

HRID 487631 reaction equation
O[C@@H:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:4]=2[C@H:3]1[N:16]1[CH:21]=[C:20]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH:19]=[CH:18][C:17]1=[O:31].[H-].[Na+]>O1CCCC1>[C:14]([C:12]1[CH:11]=[CH:10][C:5]2[O:6][C:7]([CH3:9])([CH3:8])[CH:2]=[C:3]([N:16]3[CH:21]=[C:20]([CH2:22][O:23][Si:24]([C:27]([CH3:28])([CH3:30])[CH3:29])([CH3:25])[CH3:26])[CH:19]=[CH:18][C:17]3=[O:31])[C:4]=2[CH:13]=1)#[N:15]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 131718357HCID 131718357, compound

Product 1

HCID 21746905HCID 21746905, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of anhydrous tetrahydrofuran, is dissolved 1.32 g of trans-3-hydroxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-5-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 12. Then, 0.12 g of 60% oily sodium hydride is added to the solution at room temperature, and reacted under reflux for 3 hours. The reaction mixture is concentrated under reduced pressure, and the residue is mixed with ethyl acetate and water and extracted with the ethyl acetate. The organic layer is successively washed with water and 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 1/3 mixture of ethyl acetate/methylene chloride as a developing solvent to obtain 1.16 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-5-t-butyldimethylsilyloxymethyl-1-pyridinyl}-2H-benzo[b]pyran.

Workup

  1. customreacted
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. additionthe residue is mixed with ethyl acetate and water
  5. extractionextracted with the ethyl acetate
  6. washThe organic layer is successively washed with water and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe inorganic matter is filtered off
  9. concentrationthe filtrate is concentrated under reduced pressure
  10. customThe residue is purified by silica gel column chromatography
  11. addition1/3 mixture of ethyl acetate/methylene chloride as a developing solvent

Sources & evidence

ORD record
ord-c2a85e82330f46069c590487029891cd
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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