Acetyl chloride → HCID 69012019, compound
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[C:9](Cl)(=[O:11])[CH3:10].[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[C:25]1([Mg]Cl)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[C:9]([N:6]1[CH:7]=[CH:8][C:3](=[O:2])[CH2:4][CH:5]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:11])[CH3:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 4-methoxypyridine (45.871 mmol, 1.0 eq.) in dry tetrahydro-furan (200 ml) was added acetyl chloride (45.871 mmol, 1.0 eq.), followed by TMSOTf (45.871 mmol, 1.0 eq.) at room temperature. The reaction mixture was cooled to −78° C. and stirred for 1 h. PhMgCl (3.0 eq., 2M solution in THF) was added dropwise to the reaction mixture at −78° C. and mixture was stirred at same temperature for additional 1 h. The reaction mixture was quenched with 2M HCl and warmed to room temperature. The mixture was extracted with ethyl acetate, dried over sodium sulfate and solvent was evaporated under reduced pressure to get crude product which was purified by column chromatography. Yield: 65%
Workup
- stirringmixture was stirred at same temperature for additional 1 h
- customThe reaction mixture was quenched with 2M HCl
- temperaturewarmed to room temperature
- extractionThe mixture was extracted with ethyl acetate
- dry with materialdried over sodium sulfate and solvent
- customwas evaporated under reduced pressure
- customto get crude product which
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-82a14cff3a18420cb0c294610ccc9ee7
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268814B2
Reaction notes
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