Acetyl chloride → 1-{2-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-cyclopropyl-phenyl}-3-trimethylsilyoxy-2-aza-1,3-butadiene
Reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:20][CH2:19]2)=[CH:14][C:11]=1C=O)([CH3:4])([CH3:3])[CH3:2].ClC1C=[C:26](C=CC=1)[CH:27]=[O:28].[CH3:32][Si:33]([CH3:40])([CH3:39])N[Si](C)(C)C.C([Li])CCC.C[Si](Cl)(C)C.[CH2:51]([N:53](CC)CC)C.C(Cl)(=O)C>>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:19][CH2:20]2)=[CH:14][C:11]=1[CH:51]=[N:53][C:27]([O:26][Si:33]([CH3:40])([CH3:39])[CH3:32])=[CH2:28])([CH3:2])([CH3:3])[CH3:4]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-cyclopropyl-benzaldehyde (3.36 g, 10.5 mmol) prepared in example 130b 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, 4.2 mL, 10.5 mmol), trimethylsilyl chloride (1.33 mL, 10.5 mmol), triethylamine (1.9 mL, 13.6 mmol) and acetyl chloride (0.97 mL, 13.6 mmol) to give 1-{2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-cyclopropyl-phenyl}-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.
Sources & evidence
- ORD record
- ord-3ebb4c2d908c45199a67de24fc6d0aa0
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
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