Toluene → HCID 70044288, Verbindung

HRID 2081846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2081846
[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[O:18][C:19]([CH3:22])=[CH:20][CH:21]=2)/[C:12](OC)=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>O1CCCC1>[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[O:18][C:19]([CH3:22])=[CH:20][CH:21]=2)/[CH2:12][OH:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 86746470methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(5-methyl-2-furyl)methyl-2-propenoate

Produkt 1

HCID 70044288HCID 70044288, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(5-methyl-2-furyl)methyl-2-propenoate (Example 6, Method A) (1.5 mmol) in dry tetrahydrofuran (10 mL) held at -78° C. under argon is treated dropwise with a solution of diisobutyl aluminum hydride in toluene (3.30 mmol, 2.2 mL of 1.5M). The mixture is allowed to warm to ambient temperature and stirred an additional 17 hours. Excess reducing agent is quenched with methanol and water, dilute acetic acid and methylene chloride are added, and the organic layer is washed with sodium bicarbonate solution, dried and concentrated to give the title compound.

Aufarbeitung

  1. customheld at -78° C. under argon
  2. customis quenched with methanol and water, dilute acetic acid and methylene chloride
  3. additionare added
  4. washthe organic layer is washed with sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3dcab1472e734f4cb3a034f189236211
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05185351

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