3-Ethyl-4-[(phenylmethyl)oxy]benzonitrile → HCID 68322517, compound

HRID 1505382Notes

Reaction equation

HRID 1505382 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11]CC1C=CC=CC=1)[C:6]#[N:7])[CH3:2]>CCOC(C)=O.CCO.[Pd]>[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[OH:11])[C:6]#[N:7])[CH3:2]

Participants

4

Reactant 1

HCID 569840103-Ethyl-4-[(phenylmethyl)oxy]benzonitrile2×

Product 1

HCID 68322517HCID 68322517, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

3-ethyl-4-[(phenylmethyl)oxy]benzonitrile (Intermediate 112, 334 mg) was dissolved in 15 mL of EtOAc/EtOH (2/1) and 10% mol Pd/C (0.1 equiv) was added to the solution. The resulting mixture was stirred overnight at room temperature under hydrogen gas atmosphere. The reaction mixture was filtered under argon and the solvent was removed. The residue obtained was purified by chromatography on silica gel (Companion system, 40 g Si cartridge) using as eluent a gradient cyclohexane/ethyl acetate from 100:0 to 80:20. Evaporation afforded the title compound (148 mg) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered under argon
  2. customthe solvent was removed
  3. customThe residue obtained
  4. customwas purified by chromatography on silica gel (Companion system, 40 g Si cartridge)
  5. customEvaporation

Sources & evidence

ORD record
ord-38149e990b70494a90e4f157bcd8c100
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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