4-(3,6-dihydro-2H-pyran-4-yl)benzonitrile → 4-(Tetrahydro-2H-pyran-4-yl)benzonitrile

HRID 1961439Notes

Reaction equation

HRID 1961439 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1>CCO.[Pd]>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 666330234-(3,6-dihydro-2H-pyran-4-yl)benzonitrile

Product 1

HCID 666329764-(Tetrahydro-2H-pyran-4-yl)benzonitrileYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

450 mg (2.43 mmol) 4-(3,6-dihydro-2H-pyran-4-yl)benzonitrile was dissolved in 15 ml EtOH and 50 mg 10% Pd/C was added. The reaction mixture was stirred under H2 (4 bar) over night at room temperature. The mixture was filtered through celite with EtOAc washing. The filtrate was concentrated and the crude product 340 mg (75% yield) was used directly in the next step.

Workup

  1. filtrationThe mixture was filtered through celite with EtOAc washing
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-aa96eb4e222b42e7a2776e7850b6b75c
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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