Acetic Acid → 3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzaldehyde oxime
Reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:18])([CH3:17])[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH:11]=O)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[NH2:24][OH:25].Cl.CC(O)=O>CC#N.CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].O>[C:1]([SiH2:5][O:6][C:7]([CH3:18])([CH3:17])[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH:11]=[N:24][OH:25])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzaldehyde (12.7 g, 44.6 mmol) was dissolved in CH3CN (53 mL). To this sol. was added NaHCO3 (11.2 g, 134 mmol), and the mixture was stirred vigorously for 5 min. Water (96 mL) was added and the mixture was stirred for 10 min. NH2OH—HCl (6.20 g, 89.2 mmol) was added dropwise, followed by TBAC (622 mg, 2.24 mmol). The mixture was stirred at rt for 1 h, and AcOH (4.00 mL) was added dropwise to pH 6-7. The mixture was diluted with water (100 mL), and this mixture was extracted with Et2O (3×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (15.1 g, 98%) that was used further without purification. LC-MS: tR=1.09 min; ES+: 341.13.
Workup
- stirringthe mixture was stirred for 10 min
- stirringThe mixture was stirred at rt for 1 h
- extractionthis mixture was extracted with Et2O (3×)
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customDrying the residue under high vacuum
Sources & evidence
- ORD record
- ord-b74387f8727d4468881099a4baad25f8
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799805B2
Reaction notes
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