Propargyl alcohol → 3-(3-hydroxyprop-1-ynyl)benzonitrile

HRID 1093466Notes

Reaction equation

HRID 1093466 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:29]([OH:32])[C:30]#[CH:31].C(N(C(C)C)CC)(C)C>[Cl-].[Na+].O.[Cu]I.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.C(Cl)(Cl)Cl.[Pd].[Pd].O1CCCC1>[C:5]([C:4]1[CH:3]=[C:2]([C:31]#[C:30][CH2:29][OH:32])[CH:9]=[CH:8][CH:7]=1)#[N:6]

Participants

9

Reactant 4

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 1443413-Iodobenzonitrile

Product 1

HCID 44471293-(3-hydroxyprop-1-ynyl)benzonitrile

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 3-iodobenzonitrile (10.0 g), copper(I) iodide (166 mg), triphenylphosphine (572 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (904 mg), propargyl alcohol (2.83 ml), diisopropylethylamine (30.5 ml) and tetrahydrofuran (170 ml) was stirred at room temperature for 23 hr. The reaction mixture was added to brine, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-67:33) to give the object product (5.59 g) as a brown solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-67:33)

Sources & evidence

ORD record
ord-927c351da45c48b8853096b917347772
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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