Acetyl chloride → 1-(3-Iodophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene

HRID 1728125Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([Si:14]([CH3:29])([CH3:28])[O:15][CH2:16][CH2:17]OC1C=CC(I)=CC=1C=O)(C)(C)C.C[Si]([NH:34][Si](C)(C)C)(C)C.C([Li])CCC.C[Si](Cl)(C)C.C(N(CC)CC)C.C(Cl)(=O)C>>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[N:34][C:16]([O:15][Si:14]([CH3:29])([CH3:28])[CH3:10])=[CH2:17])[CH:7]=[CH:8][CH:9]=1

Participants

Reactant 7

HCID 6367Acetyl chloride

HCID 6397Chlorotrimethylsilane

HCID 8471Triethylamine

HCID 13838Hexamethyldisilazane

HCID 2526103-Iodobenzaldehyde

HCID 57565907HCID 57565907, compound

HCID 178418339Butyllithium

Product 1

HCID 765681791-(3-Iodophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene

Procedure

In a manner similar to the method described in example 190b, 3-iodo-benzaldehyde (0.9 g, 3.88 mmol) (Aldrich) 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 (0.62 g, 3.88 mmol), n-butyllithium (2.5 M, 1.6 mL, 3.88 mmol), trimethylsilyl chloride (0.42 g, 3.88 mmol), triethylamine (0.53 g, 5.28 mmol) and acetyl chloride (0.41 g, 5.28 mmol) to give 1-(3-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-31849414807b4eb0bc90764cd4b01e3d
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Reaction notes

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