Tetrahydro-4H-pyran-4-one → HCID 86716198, compound

HRID 512171Notes

Reaction equation

HRID 512171 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[O:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1>CCO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[C:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)[C:10]#[N:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 2415824-Chlorobenzyl cyanideHCID 5360545Sodium2×

Product 1

HCID 86716198HCID 86716198, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (152 mg, 6.6 mmol) was added into EtOH (10 ml) and stirred at room temperature for 20 minutes. 2-(4-Chlorophenyl)acetonitrile (500 mg, 3.3 mmol) was added to the solution, after all the sodium had dissolved, and the reaction was stirred at room temperature for 0.5 h. To the resulting mixture was added dihydro-2H-pyran-4(3H)-one (330 mg, 3.3 mmol) and stifled at room temperature for 1.5 h. The solvent was removed. To the residue was added water and extracted with EtOAc (3×20 mL). The combined organic solution were dried over Na2SO4 and concentrated to give crude product, which was purified by flash column chromatography (petroleum ether: EtOAc=10:1) to give compound 2-(4-chlorophenyl)-2-(dihydro-2H-pyran-4(3H)-ylidene)acetonitrile (300 mg) which was used for the next step without further purification.

Workup

  1. stirringthe reaction was stirred at room temperature for 0.5 h
  2. waitstifled at room temperature for 1.5 h
  3. customThe solvent was removed
  4. additionTo the residue was added water
  5. extractionextracted with EtOAc (3×20 mL)
  6. dry with materialThe combined organic solution were dried over Na2SO4
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customwas purified by flash column chromatography (petroleum ether: EtOAc=10:1)

Sources & evidence

ORD record
ord-bf333735fb2748acac8d9e2a37b5b8d4
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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