Water → HCID 19092538, compound

HRID 487639Notes

Reaction equation

HRID 487639 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][C:19]([CH2:22][CH2:23]O[Si](C(C)(C)C)(C)C)=[CH:18][C:17]1=[O:32].[H-].[Na+].O>O1CCCC1>[C:14]([C:12]1[CH:11]=[CH:10][C:5]2[O:6][C:7]([CH3:8])([CH3:9])[CH:2]=[C:3]([N:16]3[CH:21]=[CH:20][C:19]([CH:22]=[CH2:23])=[CH:18][C:17]3=[O:32])[C:4]=2[CH:13]=1)#[N:15]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 131718359HCID 131718359, compound

Product 1

HCID 19092538HCID 19092538, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 105 ml of anhydrous tetrahydrofuran, is dissolved 3.18 g of trans-3-hydroxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(2-t-butyldimethylsilyloxyethyl)-1-pyridinyl}-2H-benzo[b]pyran obtained in Example 23. Then, 0.28 g of 60% oily sodium hydride is added to the solution at room temperature and reacted under reflux for one hour. After stopping the reaction by adding water, the reaction mixture is extracted with ether. 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 1/4 mixture of ethyl acetate/methylene chloride as a developing solvent to obtain 2.01 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-vinyl-1-pyridinyl)-2H-benzo[b]pyran.

Workup

  1. customreacted
  2. temperatureunder reflux for one hour
  3. customthe reaction
  4. extractionthe reaction mixture is extracted with ether
  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. addition1/4 mixture of ethyl acetate/methylene chloride as a developing solvent

Sources & evidence

ORD record
ord-613c2fe9f44c47c98c7e2c754ceffee1
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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