Ethyl Acetate → HCID 21711561, compound

HRID 2080051Notes

Reaction equation

HRID 2080051 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[H-].[Na+].C1(C)C=CC(P(C2C=CC(C)=CC=2)[C:19]2(P(C3C=CC(C)=CC=3)C3C=CC(C)=CC=3)[CH2:28][CH:27]=[C:26]3[C:21](C=CC=C3)=[C:20]2[C:29]2[C:38]3C(=CC=CC=3)C=CC=2)=CC=1.C(OCC)(=[O:64])C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:20]1([CH:29]([O:64][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH3:38])[CH:21]=[CH:26][CH:27]=[CH:28][CH:19]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 12162Benzonitrile, 4-bromo-HCID 24758Sodium hydrideHCID 86612476HCID 86612476, compound

Product 1

HCID 21711561HCID 21711561, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromobenzonitrile (500 mg, 2.75 mmol) and S-(−)-α-phenylethylalcohol (403 mg, 3.30 mmol) in toluene (5 mL) were added sodium hydride (220 mg, 5.49 mmol; 60% in oil), tris(dibenzylideneacetone)dipalladium(0) (38 mg, 0.0413 mmol) and 2,2-bis(di-p-tolylphosphino)-1,1-binaphthyl (67 mg, 0.099 mmol), and the solution was stirred at 70° C. for 4 hours. The reaction solution was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and 4-(1-phenyl-ethoxy)-benzonitrile (159 mg, 26%) was obtained as a colorless oil.

Workup

  1. customwas allowed to room temperature
  2. customfor partitioning
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-21e4c2087cdb4b4fb20259a3e3a4fd0e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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