Water → 3-(Dec-1-en-1-yl)pyridine
Reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[CH3:6][N:7](P(N(C)C)(N(C)C)=O)[CH3:8].N1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)C=1.O.[CH2:26]1[CH2:30]O[CH2:28][CH2:27]1>>[CH:19]([C:20]1[CH:6]=[N:7][CH:8]=[CH:22][CH:21]=1)=[CH:23][CH2:5][CH2:4][CH2:3][CH2:2][CH2:30][CH2:26][CH2:27][CH3:28]Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution of 40 g (7.3 mmol) of 1-triphenylphosphononyl bromide dissolved in 20 ml of THF was cooled to -78° C. and 2.0 ml (2.6M in hexane, 5.2 mmol) of n-BuLi was added dropwise. This was followed by the dropwise addition of 4.5 ml (5.5. eq., 26 mmol) of HMPA. The solution was stirred for 5 minutes. Then a solution of 500 mg (4.70 mmol) of 3-pyridinecarboxaldehyde in 10 ml THF was added. The resulting solution was warmed to room temperature and stirred for 2 hours. Water was added to the reaction and this was extracted with Et2O. The organic layer was washed with saturated NH4Cl, followed by saturated NaCl and dried (Na2SO4). Hexanes were added to the resulting residue, decanted and concentrated. The crude material was purified by flash chromatography (9×3 cm, silica gel, 1:1 hexanes/EtOAc) to yield 777 mg (77%) of title pyridine as a yellow oil.
Workup
- temperatureThe resulting solution was warmed to room temperature
- stirringstirred for 2 hours
- extractionthis was extracted with Et2O
- washThe organic layer was washed with saturated NH4Cl
- dry with materialdried (Na2SO4)
- additionHexanes were added to the resulting residue
- customdecanted
- concentrationconcentrated
- customThe crude material was purified by flash chromatography (9×3 cm, silica gel, 1:1 hexanes/EtOAc)
- customto yield 777 mg (77%) of title pyridine as a yellow oil
Sources & evidence
- ORD record
- ord-8bd2a3908d894299aa56d1184ebcebfa
- Source dataset
- uspto-grants-1985_11
- Patent number
- US04555520
Reaction notes
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