Propanal → HCID 18509424, compound
Reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=2)[CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.[CH:33](=[O:36])[CH2:34][CH3:35].[Cl-].[NH4+]>>[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:14]=[C:15]([CH:33]([OH:36])[CH2:34][CH3:35])[CH:16]=[CH:17][CH:18]=2)[CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- -30 °C
Procedure
Compound 78 (2.00 g; 5.78 mmol) was dissolved in tetrahydrofran (20 ml). While the solution was stirred at −30° C. under nitrogen atmosphere, n-butyl lithium in n-hexane (1.56 M: 3.70 ml; 5.77 mmol) was added dropwise, followed by stirring for 5 minutes. The mixture was cooled to −75° C., and propionaldehyde (1 ml) was slowly added dropwise thereto. The resultant mixture was brought to room temperature over 2 hours, and the reaction was stopped by dropwise addition of saturated aqueous ammonium chloride solution, followed by extraction with diethyl ether (100 ml). The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), to thereby yield 1.08 g of the target compound as yellow oily matter (yield: 57.4%).
Workup
- stirringby stirring for 5 minutes
- temperatureThe mixture was cooled to −75° C.
- extractionfollowed by extraction with diethyl ether (100 ml)
- washThe organic layer was washed with saturated brine
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)
Sources & evidence
- ORD record
- ord-1ff0efe6dd604172a47285a9adfb12ba
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06586633B1
Reaction notes
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