Diisobutylaluminum hydride → 1,3-Dihydro-5-(hydroxymethyl)-2H-benzimidazol-2-one

HRID 892346Notes

Reaction equation

HRID 892346 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11](OC)=[O:12])=[CH:10][C:4]=2[NH:3]1.CC(C[AlH]CC(C)C)C>C1COCC1>[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:4]=2[NH:3]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 10352553methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate

Product 1

HCID 145183581,3-Dihydro-5-(hydroxymethyl)-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

24.6 g (0.128 mol) of 20a are suspended in THF and stirred with 624.8 ml (0.768 mol) of DIBAL (20% strength solution in toluene) at -70° C. overnight in analogy to Example 1a.

Sources & evidence

ORD record
ord-4fd945ec6cfa414a82b6540699ada811
Source dataset
uspto-grants-1992_06
Patent number
USRE033948

Reaction notes

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