Propargyl alcohol → 2-Propyn-1-ol, 3-(3-methylphenyl)-

HRID 1093519Notes

Reaction equation

HRID 1093519 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:28]([OH:31])[C:29]#[CH:30].C(N(C(C)C)CC)(C)C>[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].O.O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:30]#[C:29][CH2:28][OH:31])[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 122683-IodotolueneHCID 81531Diisopropylethylamine

Product 1

HCID 229868072-Propyn-1-ol, 3-(3-methylphenyl)-

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 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-methyliodobenzene (25.1 g), copper(I) iodide (440 mg), triphenylphosphine (1.50 g), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (2.39 g), propargyl alcohol (7.50 ml), diisopropylethylamine (80.0 ml) and tetrahydrofuran (230 ml) was stirred at room temperature for 10 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give the object product (8.6 g) as a brown oil.

Workup

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

Sources & evidence

ORD record
ord-d289991932854292bd8978142ce90512
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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