Hydrochloric Acid → 1-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-isoxazol-3-yl]-ethanol
Reaction equation
N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:18])([CH3:17])[C:10]1[O:14][N:13]=[C:12]([CH:15]=[O:16])[CH:11]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:19][Al](C)C.[NH4+].[Cl-].Cl>C(Cl)Cl.CCCCCCC>[C:3]([SiH2:7][O:8][C:9]([CH3:18])([CH3:17])[C:10]1[O:14][N:13]=[C:12]([CH:15]([OH:16])[CH3:19])[CH:11]=1)([CH3:6])([CH3:4])[CH3:5]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(tert-butyl-dimethyl-silanyloxymethyl)-isoxazole-3-carbaldehyde (1.74 g, 7.22 mmol) in CH2Cl2 (72.0 mL) was treated at 0° C. with trimethylaluminum (22.0 mL of a 1M solution in heptane, 22.0 mmol). The reaction mixture was then stirred at 0° C. for 50 min. CH2Cl2 (80.0 mL) followed by sat. aq. NH4Cl (80 mL) were then added. The mixture was then treated with 1N HCl (50 mL) and the aq. layer was extracted with CH2Cl2 (100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a colorless oil: TLC:rf (7:3 hept-EA)=0.32. LC-MS-conditions 02: tR=1.01 min, [M+H]+=258.41.
Workup
- additionwere then added
- extractionthe aq. layer was extracted with CH2Cl2 (100 mL)
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
Sources & evidence
- ORD record
- ord-ab5453297ae44599b0e13c650e579ae9
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536209B2
Reaction notes
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