Acetyl chloride → 3-Trimethylsilyoxy-2-aza-1,3-butadiene

HRID 1728113Notes

Reaction equation

BrC1C=CC(O[CH2:11][CH2:12][O:13][Si:14]([C:17](C)(C)C)([CH3:16])[CH3:15])=C(C=1)C=O.C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.C[Si](Cl)(C)C.[CH2:40]([N:42](CC)CC)C.C(Cl)(=O)C>>[CH3:15][Si:14]([CH3:17])([CH3:16])[O:13][C:12](=[CH2:11])[N:42]=[CH2:40]

Participants

Reactant 6

HCID 6367Acetyl chloride

HCID 6397Chlorotrimethylsilane

HCID 8471Triethylamine

HCID 13838Hexamethyldisilazane

HCID 575662345-Bromo-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-benzaldehyde

HCID 178418339Butyllithium

Product 1

HCID 866175943-Trimethylsilyoxy-2-aza-1,3-butadiene

Procedure

In a manner similar to the method described in example 1b, 5-bromo-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-benzaldehyde (17.25 g, 48 mmol) prepared in example 130a was reacted with 1,1,1,3,3,3-hexamethyldisilazane (8.28 g, 48 mmol), n-butyllithium (2.5 M, 19.2 mL, 48 mmol), trimethylsilyl chloride (6.07 mL, 48 mmol), triethylamine (8.7 mL, 62.5 mmol) and acetyl chloride (4.53 mL, 62 mmol) to give 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as yellow oil and used for the next step without further purification.

Sources & evidence

ORD record: ord-be02360a21fb415592fc9b9af77a5a56
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Reaction notes

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