Diisobutylaluminum hydride → 5,6-Diphenylpyridine-2-carbaldehyde

HRID 12544

Reaktionsgleichung

Reaktionsgleichung von HRID 12544
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19](OCC)=[O:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH:19]=[O:20])=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 14789610Ethyl 5,6-diphenylpyridine-2-carboxylate2×

Produkt 1

HCID 214713565,6-Diphenylpyridine-2-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

General Procedure L. To a solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 145 mg, 0.48 mmol) in CH2Cl2 (5 ml) at −78° C. was added DIBAL-H (0.72 ml, 0.72 mmol, 1.0 M in Toluene) and the mixture was stirred between −78° C. and −60° C. for 1 hour under argon. The reaction was quenched with aq, NH4Cl, diethyl ether and 400 mg Celite were added, and the mixture was stirred at room temperature 30 min. The solid was filtered off and rinsed with ether, and the combined filtrate was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, 15% ethyl acetate in hexane) to produce the title compound.

Aufarbeitung

  1. customThe reaction was quenched with aq, NH4Cl, diethyl ether and 400 mg Celite
  2. additionwere added
  3. stirringthe mixture was stirred at room temperature 30 min
  4. filtrationThe solid was filtered off
  5. washrinsed with ether
  6. concentrationthe combined filtrate was concentrated in vacuo
  7. customthe residue was purified by column chromatography (silica gel, 15% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f2ac45d32fa641e1bc045452d34d6cd4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728014B2

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