Acetyl chloride → 3-Trimethylsilyoxy-2-aza-1,3-butadiene
Reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH2:7][CH2:8]OC1C=CC(Cl)=CC=1C=O)(C)(C)C.C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.C[Si](Cl)(C)C.[CH2:40]([N:42](CC)CC)C.C(Cl)(=O)C>>[CH3:1][Si:5]([CH3:20])([CH3:19])[O:6][C:7](=[CH2:8])[N:42]=[CH2:40]Participants
7
Procedure
In a manner similar to the method described in example 1b, 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-benzaldehyde (5.2 g, 17 mmol) prepared in example 131a was reacted with 1,1,1,3,3,3-hexamethyldisilazane (2.4 g, 15 mmol), n-butyllithium (2.5 M, 6 mL, 15 mmol), trimethylsilyl chloride (1.6 g, 15 mmol), triethylamine (1.6 g, 20 mmol) and acetyl chloride (1.5 g, 20 mmol) to give 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as yellow oil and used for the next step without further purification.
Sources & evidence
- ORD record
- ord-aa111af147fa40a2b9e46e0b58cbe7c2
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
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