Diisobutylaluminum hydride → HCID 22285566, compound

HRID 1062441Notes

Reaction equation

HRID 1062441 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH:10]=[C:11]([C:13](OCC)=[O:14])[N:12]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[CH:10]=[C:11]([CH:13]=[O:14])[N:12]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 22285380HCID 22285380, compound

Product 1

HCID 22285566HCID 22285566, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of ethyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate (200 mg, 0.51 mmol) in toluene (10 mL) at −78° C. was added DIBAH (2.0 mL) in toluene dropwise. The resulting solution was stirred at rt, quenched with 1N HCl (0.5 mL). The organic layer was washed with 1N HCl (5 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (50% EtOAc in hexane) to give the product (62 mg, 38% yield). LC-MS m/z 317.0 (MH+), retention time: 2.75 min (method 1).

Workup

  1. customquenched with 1N HCl (0.5 mL)
  2. washThe organic layer was washed with 1N HCl (5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-828f078a73d54489979c840ecee5e595
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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