Acetyl chloride → HCID 76568111, compound

HRID 1728142Notes

Reaction equation

HRID 1728142 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.[C:12]([Si:16]([CH3:31])([CH3:30])[O:17][CH2:18][CH2:19]OC1C=CC(I)=CC=1C=O)(C)(C)C.C[Si]([NH:36][Si](C)(C)C)(C)C.C([Li])CCC.C[Si](Cl)(C)C.C(N(CC)CC)C.C(Cl)(=O)C>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[N:36][C:18]([O:17][Si:16]([CH3:31])([CH3:30])[CH3:12])=[CH2:19])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

8

Reactant 7

HCID 6367Acetyl chlorideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 13838HexamethyldisilazaneHCID 27738751-Benzofuran-5-carbaldehydeHCID 57565907HCID 57565907, compoundHCID 178418339Butyllithium

Product 1

HCID 76568111HCID 76568111, compound

Procedure

In a manner similar to the method described in example 190b, 1-benzofuran-5-carbaldehyde (1.2 g, 10 mmol) (Maybr-INT) 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 (1.6 g, 10 mmol), n-butyllithium (2.5 M, 4 mL, 10 mmol), trimethylsilyl chloride (1.1 g, 10 mmol), triethylamine (1.36 g, 13.6 mmol) and acetyl chloride (1 g, 13.6 mmol) to give crude 1-(1-benzofuran-5-yl)-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-df9eede6dca24d7e8436d9c3eadedab4
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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