Diisobutylaluminumhydride → 1-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethyl)-1h-pyrazole-3,5dimethanol
Reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]([C:16](OCC)=[O:17])=[CH:14][C:13]([C:21](OCC)=[O:22])=[N:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:15]([CH2:16][OH:17])=[CH:14][C:13]([CH2:21][OH:22])=[N:12]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of diethyl 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1H-pyrazole-3,5-dicarboxylate (0.74 g, 2 mmol) in methylene chloride (8 ml), under nitrogen, was added 12 ml of a 1.0 M solution of diisobutylaluminum hydride in methylene chloride at 0° C. After stirring at 0° C. for 0.5 hr, the mixture was warmed to room temperature for 0.5 hr. It was then quenched with 15 ml of saturated ammonium chloride solution and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, and evaporated to give 0.44 g of a white solid; mp 82-83° C.; MS m/e 287 (MH+).
Workup
- temperaturethe mixture was warmed to room temperature for 0.5 hr
- customIt was then quenched with 15 ml of saturated ammonium chloride solution
- extractionextracted with ethyl acetate
- extractionThe organic extract
- washwas washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-1e1c50bfafd847f9806aa2bf345247a7
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812014B2
Reaction notes
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