4-(3,6-dihydro-2H-pyran-4-yl)benzonitrile → 4-(Tetrahydro-2H-pyran-4-yl)benzonitrile
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe mixture was filtered through celite with EtOAc washing
- 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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