Acetyl chloride → 1-(5-Iodo-2-nitrophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene

HRID 1095069Notes

Reaction equation

[I:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=O.[C:13]([Si:17]([CH3:32])([CH3:31])[O:18][CH2:19][CH2:20]OC1C=CC(I)=CC=1C=O)(C)(C)C.C[Si]([NH:37][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]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]=[N:37][C:19]([O:18][Si:17]([CH3:32])([CH3:31])[CH3:13])=[CH2:20])[CH:9]=1

Participants

Reactant 7

HCID 6367Acetyl chloride

HCID 6397Chlorotrimethylsilane

HCID 8471Triethylamine

HCID 13838Hexamethyldisilazane

HCID 137567585-Iodo-2-nitrobenzaldehyde

HCID 57565907HCID 57565907, compound

HCID 178418339Butyllithium

Product 1

HCID 666415651-(5-Iodo-2-nitrophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene

Procedure

In a manner similar to the method described in example 1d, 5-iodo-2-nitrobenzaldehyde prepared in Example 9a (4.2 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 (2.1 g, 20 mmol) and acetyl chloride (1.5 g, 20 mmol) to give crude 1-(5-Iodo-2-nitrophenyl)-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-aa22e6810838444e804f11c7b63ef4e0
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08134001B2

Reaction notes

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