4-Methoxypyridine → 4-Methoxy-3-(triisopropylsilyl)pyridine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Li+].CC([N-]C(C)C)C.CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C.[CH:37]([Si:40](Cl)([CH:44]([CH3:46])[CH3:45])[CH:41]([CH3:43])[CH3:42])([CH3:39])[CH3:38]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[Si:40]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:37]([CH3:39])[CH3:38]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -25 °C
Procedure
Following the procedure reported in JACS 1994, 116, 4719-4728, to a solution of 4-methoxypyridine (14.0 g, 128.3 mmol) in THF (150 mL) was added at −25° C., 2.0M LDA in heptane/THF/ethyl benzene (76.9 mL, 153.9 mmol). The mixture was stirred at −25° C. for 30 minutes. Triisopropylsilyl chloride (35.3 mL, 166.8 mmol) was added and the mixture was stirred at −25° C. for 15 minutes and then at room temperature for 16 hours. Water was added and the mixture was extracted with EtOAc. The extract was washed with water, brine dried over MgSO4 and concentrated to dryness. Purification of the residue by flash chromatography (hexane/ethylacetate 8:2-1:1) gave 4-methoxy-3-triisopropylsilanyl-pyridine (7.56 g, 22%) as an orange solid.
Workup
- additionwas added at −25° C.
- stirringthe mixture was stirred at −25° C. for 15 minutes
- waitat room temperature for 16 hours
- extractionthe mixture was extracted with EtOAc
- washThe extract was washed with water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated to dryness
- customPurification of the residue by flash chromatography (hexane/ethylacetate 8:2-1:1)
Sources & evidence
- ORD record
- ord-df314cae4932467eb12a3899b6d43f09
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153809B2
Reaction notes
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