Acetyl chloride → N-[(5-Chloro-2-iodophenyl)methylene]-1-[(trimethylsilyl)oxy]ethenamine

HRID 1095115Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:9]=1)[CH:7]=O.[C:11]([Si:15]([CH3:30])([CH3:29])[O:16][CH2:17][CH2:18]OC1C=CC(I)=CC=1C=O)(C)(C)C.C[Si]([NH:35][Si](C)(C)C)(C)C.C([Li])CCC.C[Si](Cl)(C)C.C(N(CC)CC)C.C(Cl)(=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:7]=[N:35][C:17]([O:16][Si:15]([CH3:30])([CH3:29])[CH3:11])=[CH2:18])[CH:9]=1

Participants

Reactant 7

HCID 6367Acetyl chloride

HCID 6397Chlorotrimethylsilane

HCID 8471Triethylamine

HCID 13838Hexamethyldisilazane

HCID 575658825-Chloro-2-iodobenzaldehyde

HCID 57565907HCID 57565907, compound

HCID 178418339Butyllithium

Product 1

HCID 66641533N-[(5-Chloro-2-iodophenyl)methylene]-1-[(trimethylsilyl)oxy]ethenamine

Procedure

In a manner similar to the method described in example 5d, 5-chloro-2-iodobenzaldehyde prepared in example 23a (3.97 g, 15 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 (2.4 g, 15 mmol), n-butyllithium (2.5 M, 6 mL, 15 mmol), trimethylsilyl chloride (1.6 g, 15 mmol), triethylamine (2 g, 20 mmol) and acetyl chloride (1.5 g, 20 mmol) to give crude 1-(5-chloro-2-iodophenyl)-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-c8cea56a1aaa4d9fa71970e006f0680b
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08134001B2

Reaction notes

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