HCID 54227624, compound → HCID 22015785, compound

HRID 353292Notes

Reaction equation

HRID 353292 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])=[CH:4][CH:3]=1>COCCOC.[Pd].O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 54227624HCID 54227624, compound

Product 1

HCID 22015785HCID 22015785, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-[2-(4-Fluorophenyl)ethenyl]benzonitrile (8.10 g, 36.3 mmol) was dissolved in ethylene glycol dimethyl ether (200 mL). Palladium on charcoal (10% Pd; 0.81 g) in H2O (1.0 mL) was added, and the reaction mixture was shaken under 60 psig H2 for 1 h. The reaction mixture was then filtered through Celite®, and the filtrate was rotary evaporated (75° C.). This provided 8.03 g (98.3%) of the product as an orange oil which crystallized on standing.

Workup

  1. filtrationThe reaction mixture was then filtered through Celite®
  2. customthe filtrate was rotary evaporated (75° C.)
  3. customThis provided 8.03 g (98.3%) of the product as an orange oil which crystallized

Sources & evidence

ORD record
ord-ca3d187923e24d20b0b04274383c0c30
Source dataset
uspto-grants-2004_06
Patent number
US06750244B2

Reaction notes

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