Pentane → HCID 14987392, compound
Reaction equation
CN(C)[CH:3]=[C:4]1[N:8]=[CH:7][CH:6]=[CH:5]1.CCC[CH2:13][CH3:14].ICCC.[C:19](=O)(O)[O-:20].[Na+]>C1COCC1.O>[CH2:3]([C:4]1[NH:8][C:7]([CH:19]=[O:20])=[CH:6][CH:5]=1)[CH2:13][CH3:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To an anhydrous solution of 6-dimethylamino-1-azafulvene dimer (125; 12.0 g, 49.1 mmol) in THF (500 ml) at -15° C. was added dropwise a solution of 5-butyllithium in pentane (1.7M; 87 ml, 147 mmol) over 5 minutes. The yellow cloudy solution was slowly warmed to 0° C. over 10 minutes and stirred at this temperature for a further 20 minutes. The resulting deep violet colored solution was treated with 1-iodopropane (19.2 ml, 196 mmol) and allowed to warm to room temperature over 2 hours. The mixture was treated with water (20 ml) and saturated aqueous sodium bicarbonate (20 ml) and refluxed for 15 hours. The mixture was extracted into methylene chloride and the organic phase was washed with saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered and concentrated to a dark liquid residue (15.2 g) by rotary evaporation. Flash chromatography (silica gel, 500 g; EtOAc/hexanes, 5/95) gave 7.85 g (60%) of the title compound as a pale brown liquid.
Workup
- temperatureto warm to room temperature over 2 hours
- temperaturerefluxed for 15 hours
- extractionThe mixture was extracted into methylene chloride
- washthe organic phase was washed with saturated aqueous sodium bicarbonate
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to a dark liquid residue (15.2 g) by rotary evaporation
Sources & evidence
- ORD record
- ord-dc43096928024cd8a5a9d0ec81233631
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05043349
Reaction notes
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