Diisobutylaluminum hydride → HCID 178432471, compound

HRID 12469Notes

Reaction equation

HRID 12469 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[N:9][C:10]=1[CH3:11])=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:11][C:10]1[N:9]=[C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[NH:7][C:6]=1[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 178470380HCID 178470380, compound

Product 1

HCID 178432471HCID 178432471, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester (280 mg) in THF (8 ml) is added DIBAL-H (3.3 ml, 1.5 M in toluene) at 0° C. The resulting solution is stirred at rt for 2 hr, and quenched with brine. The THF layer is separated and then evaporated. The residue is dissolved in EtOAc, washed with water and brine, dried and solvent evaporated to afford (5-methyl-2-naphthalen-1-yl-3H-imidazol-4-yl)-methanol.

Workup

  1. customquenched with brine
  2. customThe THF layer is separated
  3. customevaporated
  4. dissolutionThe residue is dissolved in EtOAc
  5. washwashed with water and brine
  6. customdried
  7. customsolvent evaporated

Sources & evidence

ORD record
ord-3f60c457229c49a889b0212e15c53cb0
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Reaction notes

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