Diisobutylaluminumhydride → (2-Methoxy-5-(2-methyl-2H-tetrazol-5-yl)phenyl)methanol
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[N:15][N:16]([CH3:18])[N:17]=2)=[CH:9][C:4]=1[C:5](OC)=[O:6].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[N:15][N:16]([CH3:18])[N:17]=2)=[CH:9][C:4]=1[CH2:5][OH:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Methyl 2-methoxy-5-(2-methyl-2H-tetrazol-5-yl)benzoate (130 mg, 0.52 mmol) was dissolved in methylene chloride (2 mL), cooled to −78° C. and treated with diisobutylaluminum hydride (1 M in methylene chloride, 1.5 mL, 1.5 mmol). After stirring at −78° C. for 1 h the reaction was quenched by a few drops of methanol (until no bubbling was observed) followed by addition of excess saturated sodium potassium tartarate (2 mL). The reaction was stirred at room temperature overnight, the layers were separated and the organic layer washed with brine (2×), dried over sodium sulfate and concentrated to afford 100 mg (86%). LC/MS (HPLC method 3): tR=1.68 min, 221.11 (MH)+
Workup
- customwas quenched by a few drops of methanol (until no bubbling
- additionfollowed by addition of excess saturated sodium potassium tartarate (2 mL)
- stirringThe reaction was stirred at room temperature overnight
- customthe layers were separated
- washthe organic layer washed with brine (2×)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customto afford 100 mg (86%)
Sources & evidence
- ORD record
- ord-efe227a18c6948428a28abefd3fa8714
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383821B2
Reaction notes
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