Water → Methyl 4-(3-hydroxyprop-1-ynyl)benzoate

HRID 1267454Notes

Reaction equation

HRID 1267454 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([OH:15])[C:13]#[CH:14].C(N(CC)CC)C.O>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([C:14]#[C:13][CH2:12][OH:15])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 69273Methyl 4-iodobenzoate

Product 1

HCID 4448596Methyl 4-(3-hydroxyprop-1-ynyl)benzoateYield 87.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 4-iodobenzoate (20 g, 76 mmol), propargyl alcohol (5.55 g, 99.0 mmol) and triethylamine (20 mL) in acetonitrile (200 mL) was added dichlorobis(triphenylphosphine)palladium(II) (1.55 g, 2.21 mmol), followed by Cul (454 mg, 2.38 mmol). The reaction mixture was stirred at room temperature for 24 h. Water was added and the aqueous solution was washed with EtOAc (3×). The organic solutions were combined, dried (MgSO4), filtered and concentrated. Purification by medium pressure chromatography (9:1 hexanes:EtOAc to 4:1 hexanes:EtOAc) provided 4-(3-hydroxy-prop-1-ynyl)-benzoic acid methyl ester (12.65 g).

Workup

  1. washthe aqueous solution was washed with EtOAc (3×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by medium pressure chromatography (9:1 hexanes:EtOAc to 4:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-a4f102dc50da4c33a0605fa66eee12b4
Source dataset
uspto-grants-2003_04
Patent number
US06552067B2

Reaction notes

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