Pyrrole → HCID 23051028, compound
Reaction equation
C([Li])CCC.[NH:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.Cl[CH2:12][CH2:13][CH2:14][Si:15]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]>C1COCC1>[CH2:20]([O:19][Si:15]([O:22][CH2:23][CH3:24])([O:16][CH2:17][CH3:18])[CH2:14][CH2:13][CH2:12][N:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1)[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A solution of butyllithium (1.6 M in hexane, 187 mL, 0.3 mol) is added in 1 hour to a solution of pyrrole (20 g, 0.3 mol) in THF (200 ml) cooled to −10° C. This solution is kept at 0° C. for 1 hour. 72.3 g of 3-chloropropyltriethoxysilane (0.3 mol) is added to this solution, then the temperature of the reaction mixture is raised to +65° C. for 8 hours. After the temperature of the reaction mixture has returned to 20° C., the THF is evaporated under vacuum. The raw product is taken up in cyclohexane (150 mL), the salts of lithium chloride are filtered and the aqueous solution is washed with 50 mL of distilled water. The organic phase is dried over magnesium sulfate and the solvent is evaporated under vacuum. The desired product (57.8 g) is then recovered.
Workup
- temperaturethe temperature of the reaction mixture is raised to +65° C. for 8 hours
- customhas returned to 20° C.
- customthe THF is evaporated under vacuum
- filtrationthe salts of lithium chloride are filtered
- washthe aqueous solution is washed with 50 mL of distilled water
- dry with materialThe organic phase is dried over magnesium sulfate
- customthe solvent is evaporated under vacuum
- customThe desired product (57.8 g) is then recovered
Sources & evidence
- ORD record
- ord-618b908ad9b84741b0fc61ccbb80414e
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08980392B2
Reaction notes
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