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

HRID 352605

Reaktionsgleichung

Reaktionsgleichung von HRID 352605
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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 4448596Methyl 4-(3-hydroxyprop-1-ynyl)benzoateAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e61a163fbe4346efb57e0fd0ad0b776b
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747054B2

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