Water → HCID 21746911, compound

HRID 487634Notes

Reaction equation

HRID 487634 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]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[C:17]1=[O:31].[H-].[Na+].O>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]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][Si:24]([C:27]([CH3:28])([CH3:30])[CH3:29])([CH3:25])[CH3:26])[C:17]3=[O:31])[C:4]=2[CH:13]=1)#[N:15]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 131718358HCID 131718358, compound

Product 1

HCID 21746911HCID 21746911, compoundYield 48.2%

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-3-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 16. Then, 0.12 g of 60% oily sodium hydride is added to the solution at room temperature and reacted under reflux for 3 hours. 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 1/25 mixture of methanol/methylene chloride as a developing solvent to obtain 0.61 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-3-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran.

Workup

  1. customreacted
  2. temperatureunder reflux for 3 hours
  3. customthe reaction
  4. extractionthe reaction mixture is extracted with 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 thus obtained
  10. customis purified by silica gel column chromatography
  11. addition1/25 mixture of methanol/methylene chloride as a developing solvent

Sources & evidence

ORD record
ord-5d74a6ccb02f42f4943498eef686393a
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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