Methyl iodide → (Z)-2-Bromo-3-methoxy-1-phenylundeca-1-en-4,10-diyne

HRID 1936917

Reaktionsgleichung

Reaktionsgleichung von HRID 1936917
[Br:1]/[C:2](/[CH:10]([OH:19])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])=[CH:3]\[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[K+].[CH3:22]I>CS(C)=O>[Br:1]/[C:2](/[CH:10]([O:19][CH3:22])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])=[CH:3]\[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 11324570(Z)-2-Bromo-1-phenylundeca-1-en-4,10-diyn-3-ol

Produkt 1

HCID 12052605(Z)-2-Bromo-3-methoxy-1-phenylundeca-1-en-4,10-diyneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of Compound 7 (303.0 mg, 0.96 mmol) and KOH (214.1 mg, 3.82 mmol) in DMSO (20 mL) was added MeI (271.3 mg, 1.91 mmol) followed by stirring at room temperature for 5 hours. The reaction was then quenched with saturated aqueous NH4Cl (20 mL) and extracted with EtOAc (50 mL×2). The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane) to give 214.3 mg (68 percent) of Compound 8: pale yellow oil; Rf=0.56 (20 percent EtOAc in hexane); IR (neat) 3296, 2940, 2232, 2116, 1446, 1078 cm−1; 1H NMR (300 MHz, CDCl3) δ7.68-7.65 (m, 2H), 7.38-7.25 (m, 3H), 7.29 (s, 1H), 4.76 (s, 1H), 3.42 (s, 3H), 2.36-2.31 (m, 2H), 2.26-2.21 (m, 2H), 1.95 (t, J=2.67 Hz, 1H), 1.74-1.65 (m, 4H); 13C NMR (75 MHz, CDCl3) δ135.4, 131.4, 129.8, 129.1, 128.8, 123.9, 89.2, 84.6, 77.5, 76.8, 69.3, 56.0, 28.1, 27.9, 19.0, 18.5; MS (+CI) m/z (relative intensity) 333 (M+H+, 81Br, 10), 331 (M+H+, 79Br, 12), 251 (100); HRMS (+EI) calcd for C18H19BrO 330.0619 (M+), found 330.0606.

Aufarbeitung

  1. customThe reaction was then quenched with saturated aqueous NH4Cl (20 mL)
  2. extractionextracted with EtOAc (50 mL×2)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a64cafc9a1b54542b6ca7854cb9fcd89
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06391916B1

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