Acetyl chloride → 1-{2-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-ethyl-phenyl}-3-trimethylsilyoxy-2-aza1,3-butadiene
Reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][C:11]=1[CH:12]=O)([CH3:4])([CH3:3])[CH3:2].ClC1C=[C:25](C=CC=1)[CH:26]=[O:27].[CH3:31][Si:32]([CH3:39])([CH3:38])N[Si](C)(C)C.C([Li])CCC.C[Si](Cl)(C)C.C([N:52](CC)CC)C.C(Cl)(=O)C>>[Si:5]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][C:11]=1[CH:12]=[N:52][C:26]([O:25][Si:32]([CH3:39])([CH3:38])[CH3:31])=[CH2:27])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:21])[CH3:20]Participants
8
Reactant 7
Product 1
Procedure
In a manner similar to the method described in example 1b, 2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-5-ethyl-benzaldehyde (3.24 g, 10.5 mmol) prepared in example 185a was used as the starting material in place of 3-chloro-benzaldehyde to react with 1,1,1,3,3,3-hexamethyldisilazane (2.18 mL, 10.5 mmol), n-butyllithium (2.5 M, 4 mL, 10.5 mmol), trimethylsilyl chloride (1.1 g, 10 mmol), triethylamine (1.4 g, 13 mmol) and acetyl chloride (1.0 g, 13 mmol) to give 1-{2-[2-(tert-butyl-dimethylsilanyloxy)-ethoxy]-5-ethyl-phenyl}-3-trimethylsilyoxy-2-aza-1,3-butadiene as yellow gum and used for the next step without further purification.
Sources & evidence
- ORD record
- ord-7836ce0e7c8945d5873c9b43482aa9b4
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
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