Ethyl ketone → 1-(1-Ethylpropenyl)pyrrolidine
Reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][CH2:7][C:8](=O)[CH2:9][CH3:10]>CCCCC.[Ti](Cl)(Cl)(Cl)Cl>[CH2:9]([C:8]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:7][CH3:6])[CH3:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
99 g (1.39 mole) of pyrrolidine dissolved in 460 ml of n-pentane were added clropwise to 40 g (0.464 mole) of 3-pentanone dissolved in 1600 ml of n-pentane, and the solution was cooled to 0° C. in an ice bath. 48.4 g (0.255 mole) of titanium tetrachloride dissolved in 480 ml of n-pentane were added dropwise at 0° C.-10° C. within one hour, the mixture was stirred for two further hours at RT, and the suspension was filtered. The filtrate was concentrated by evaporation on a rotary evaporator (500 to 10 mbar), and 44.3 g of 1-(1-ethylpropenyl)pyrrolidine (68.6% of theory) were obtained in this way.
Workup
- additionwere added dropwise at 0° C.-10° C. within one hour
- filtrationthe suspension was filtered
- concentrationThe filtrate was concentrated by evaporation on a rotary evaporator (500 to 10 mbar)
Sources & evidence
- ORD record
- ord-6b8ae241906c46d1b8580987ef29e0dc
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06410790B1
Reaction notes
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