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

HRID 12544

Reaction equation

HRID 12544 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 214713565,6-Diphenylpyridine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f2ac45d32fa641e1bc045452d34d6cd4
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Linked notes

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