Methyl 4-iodobenzoate → Methyl 4-(5-hydroxypentynyl)benzoate

HRID 2098368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098368
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:17])[CH2:13][CH2:14][C:15]#[CH:16]>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.[Cu]I>[OH:17][CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 69273Methyl 4-iodobenzoateHCID 793464-Pentyn-1-ol

Produkt 1

HCID 11974394Methyl 4-(5-hydroxypentynyl)benzoateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Methyl 4-iodobenzoate (13.1 g, 60 mmol), PdCl2(PPh3)2 (2.0 g, 3 mmol), and CuI (855 mg, 4.5 mmol) were added to TEA (60 mL). The mixture is degassed while stirring by bubbling N2 vigorously into the solution. Pent-4-yn-1-ol (5.5 g, 66 mmol) was added by syringe. The mixture was heated at 90° C. overnight. After cooling, the crude mixture was concentrated by rotary evaporation and pumped on the high vacuum for 1 h. The oil was dissolved in DCM and adsorbed onto Celite followed by purification by chromatography (gradient 10-100% EtOAc/Hexanes) to give the title compound as a light yellow powder (9 g, 69%). 1H NMR (400 MHz, CDCl3) δ 7.95 (dd, 2H, J=9.0, 1.5 Hz), 7.44 (dd, 2H, J=9.0, 1.5 Hz), 3.90 (s, 3H), 3.85 (m, 2H), 2.57 (t, 2H, J=5.5 Hz), 1.87 (m, 2H), 1.42 (t, 1H, J=5.5 Hz); ES/MS calcd. for C13H16O3+ 219.1, found m/z=219 (M+H)+.

Aufarbeitung

  1. customThe mixture is degassed
  2. customby bubbling N2 vigorously into the solution
  3. temperatureAfter cooling
  4. concentrationthe crude mixture was concentrated by rotary evaporation
  5. dissolutionThe oil was dissolved in DCM
  6. customfollowed by purification by chromatography (gradient 10-100% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7d35fcf793cd43128768f8e2c2acb7c4
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450490B2

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