Acetyl chloride → 1-[5-Fluoro-2-(cyclopentyloxy)-phenyl]-3-trimethylsilanyloxy-2-aza-1,3-butadiene

HRID 1095188Notes

Reaction equation

HRID 1095188 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:6]([CH:9]=1)[CH:7]=O.[Li+].C[Si]([N-:21][Si](C)(C)C)(C)C.[C:26](Cl)(=[O:28])[CH3:27].Cl[Si:31]([CH3:34])([CH3:33])[CH3:32]>C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:6]([CH:7]=[N:21][C:26]([O:28][Si:31]([CH3:34])([CH3:33])[CH3:32])=[CH2:27])[CH:9]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 6397ChlorotrimethylsilaneHCID 2733832Lithium HexamethyldisilazideHCID 577432202-Cyclopentyloxy-5-fluoro-benzaldehyde

Product 1

HCID 666406341-[5-Fluoro-2-(cyclopentyloxy)-phenyl]-3-trimethylsilanyloxy-2-aza-1,3-butadiene

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a manner similar to the method described in Example 112b, 5-fluoro-2-(cyclopentyloxy)-benzaldehyde was treated with LHMDS, acetyl chloride, triethylamine and chloro-trimethyl-silane to give the desired compound, which was directly used for the next step.

Sources & evidence

ORD record
ord-8714a0fe74394f0aa0d3ae266cf8f268
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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