Acetyl chloride → 3-Trimethylsilyoxy-2-aza-1,3-butadiene
Reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][CH2:7][CH2:8]OC1C(OC)=CC(I)=CC=1C=O)(C)(C)C.C([Si](C)(C)OCCOC1C=CC(I)=CC=1C=O)(C)(C)C.C[Si](N[Si](C)(C)C)(C)C.C([Li])CCC.C[Si](Cl)(C)C.[CH2:62]([N:64](CC)CC)C.C(Cl)(=O)C>>[CH3:1][Si:5]([CH3:22])([CH3:21])[O:6][C:7](=[CH2:8])[N:64]=[CH2:62]Participants
8
Reactant 7
Product 1
Procedure
In a manner similar to the method described in example 190b, 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-iodo-3-methoxy-benzaldehyde (4.58 g, 11 mmol) was used as the starting material in place of 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-iodo-benzaldehyde to react with 1,1,3,3,3-hexamethyldisilazane (2.18 mL, 11 mmol), n-butyllithium (2.5 M, 4.2 mL, 11 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 crude 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-iodo-3-methoxy-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-ba20a7a29a0948d8bf855a5a7e4dcb97
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
Loading…