4-Ethylbenzaldehyde → HCID 69220218, compound
Reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.CCCCC.C([Li])(C)(C)C.[CH2:26]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=1)[CH3:27].[Cl-].[NH4+]>CCOCC.O1CCCC1>[CH2:26]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]([C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[O:7][CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1])[OH:33])=[CH:30][CH:29]=1)[CH3:27]Participants
Conditions
- Temperature
- -70 °C
Procedure
Next, to a mixture of 3-[2-(trimethylsilyl)ethoxymethoxy]pyridine (23.0 g, 102 mmol) and tetrahydrofuran (400 ml), a 1.47 mol/L t-butyllithium n-pentane solution (80 ml, 118 mmol) was added dropwise at −70° C. over 25 minutes. After stirring at −70° C. for 1 hour, an ether solution of 4-ethylbenzaldehyde (17.7 g, 132 mmol) was added over 25 minutes. The reaction mixture was stirred at −70° C. for 2 hours and at room temperature for 2 hours. After warming to room temperature, the reaction mixture was poured into saturated aqueous ammonium chloride and extracted with ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50) to give (4-ethylphenyl)-[3-[2-(trimethylsilyl)ethoxymethoxy]pyridin-4-yl]-methanol (20.1 g, 55%) as a light-yellow powder.
Workup
- stirringThe reaction mixture was stirred at −70° C. for 2 hours and at room temperature for 2 hours
- temperatureAfter warming to room temperature
- extractionextracted with ether
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50)
Sources & evidence
- ORD record
- ord-09f204d42e804c489412282411e3cc7d
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07439232B2
Reaction notes
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