Diisobutylaluminumhydride → HCID 59682036, Verbindung

HRID 1394653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394653
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([C:24]3[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[C:26]([CH:33]([CH3:35])[CH3:34])[C:25]=3[O:36][CH2:37][CH3:38])=[CH:22][N:23]=2)[CH:20]=1)=O>ClCCl>[CH2:37]([O:36][C:25]1[C:26]([CH:33]([CH3:34])[CH3:35])=[CH:27][C:28]([CH:30]([CH3:32])[CH3:31])=[CH:29][C:24]=1[C:21]1[N:19]2[CH:20]=[C:15]([CH2:13][OH:12])[CH:16]=[CH:17][C:18]2=[N:23][CH:22]=1)[CH3:38]

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 59682038HCID 59682038, Verbindung

Produkt 1

HCID 59682036HCID 59682036, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Diisobutylaluminum hydride (2.4 ml, 1M soln., 2.4 mmol) was added dropwise to a solution of 3-(2-ethoxy-3,5-diisopropyl-phenyl)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (300 mg, 0.79 mmol) in dichloromethane (10 mL) which had been cooled to −78° C. under a nitrogen atmosphere. After the addition was complete, the reaction was kept at −78° C. for 4 h, then quenched with with methanol (10 mL). After addition of the methanol, the mixture was poured into water, filtered and the solution evaporated to a residue. The residue was purified by silica gel chromatography (2.5% MeOH in dichloromethane) to give [3-(2-ethoxy-3,5-diisopropyl-phenyl)-imidazo[1,2-a]pyridin-6-yl]-methanol as a clear glass (102 mg, 38%). 1H NMR (250 MHz, CDCl3): δ 8.01 (s, 1H), 7.70 (bs, 1H), 7.64 (d, 1H, J=9.4), 7.24 (m, 2H), 7.12 (d, 1H, J=0.62), 4.73 (s, 1H), 3.45 (m, 1H), 3.35 (q, 2H, J=7.0), 1.34 (s, 3H), 1.31 (s, 3H), 1.30 (s, 3H), 1.29 (s, 3H), 0.84 (t, 3H, J=7.0), MS [EI+] 353 (M+H)+.

Aufarbeitung

  1. additionAfter the addition
  2. customquenched with with methanol (10 mL)
  3. additionAfter addition of the methanol
  4. additionthe mixture was poured into water
  5. filtrationfiltered
  6. customthe solution evaporated to a residue
  7. customThe residue was purified by silica gel chromatography (2.5% MeOH in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-f0fab459e995413c8d3f8a628a227e25
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348359B2

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