Acetyl chloride → HCID 76568128, compound

HRID 1728134Notes

Reaction equation

HRID 1728134 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[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>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:7]=[N:35][C:17]([O:16][Si:15]([CH3:30])([CH3:29])[CH3:11])=[CH2:18])[CH:9]=1

Participants

8

Reactant 7

HCID 6367Acetyl chlorideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 13838HexamethyldisilazaneHCID 57565907HCID 57565907, compoundHCID 575661265-Iodo-2-methylbenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 76568128HCID 76568128, compound

Procedure

In a manner similar to the method described in example 190b, 5-iodo-2-methylbenzaldehyde prepared in example 198a (5.4 g, 22 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 (3.53 g, 22 mmol), n-butyllithium (2.5 M, 8.8 mL, 22 mmol), trimethylsilyl chloride (2.22 g, 22 mmol), triethylamine (3 mL, 30 mmol) and acetyl chloride (2.34 g, 30 mmol) to give crude 1-(5-iodo-2-methylphenyl)-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-d0de2bbe5e484b118bf9055fc0ec5fee
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…