Dimethylformamide → 1-(Triisopropylsilyl)-1H-pyrrole-3-carbaldehyde
Reaction equation
Br[C:2]1[CH:6]=[CH:5][N:4]([Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])[CH:3]=1.C([Li])CCC.CN([CH:25]=[O:26])C>C1COCC1>[CH:8]([Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[N:4]1[CH:5]=[CH:6][C:2]([CH:25]=[O:26])=[CH:3]1)([CH3:10])[CH3:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 3-bromo-1-(triisopropylsilyl)-1H-pyrrole (2.0 g, 6.61 mmol) in THF (30 mL) was added n-butyllithium (2.5 M in hexanes, 3.4 mL, 8.60 mmol) at −78° C. The mixture was stirred at −78° C. for 10 min then DMF (0.76 mL, 9.92 mmol) was added and the mixture was warmed to 0° C. over 1 hour. The reaction mixture was quenched by saturated NH4Cl and extracted with EtOAc (200 mL). The organic phase was washed with brine then dried (MgSO4), filtered and concentrated to dryness. The residue was purified by column chromatography (silica, 0-10% EtOAc in hexanes) to afford the sub-title compound (1.65 g, 100%).
Workup
- temperaturethe mixture was warmed to 0° C. over 1 hour
- customThe reaction mixture was quenched by saturated NH4Cl
- extractionextracted with EtOAc (200 mL)
- washThe organic phase was washed with brine
- dry with materialthen dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated to dryness
- customThe residue was purified by column chromatography (silica, 0-10% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-a6c713ed4109427bb350d11e93a60371
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324264B1
Reaction notes
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