Acetyl chloride → 1-[5-Fluoro-2-(tetrahydro-pyran-4-yloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

HRID 1095180Notes

Reaction equation

HRID 1095180 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:6]([CH:9]=1)[CH:7]=O.[Li+].C[Si]([N-:22][Si](C)(C)C)(C)C.[C:27](Cl)(=[O:29])[CH3:28].Cl[Si:32]([CH2:37]C)([CH2:35]C)[CH2:33]C>C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:6]([CH:7]=[N:22][C:27]([O:29][Si:32]([CH3:37])([CH3:35])[CH3:33])=[CH2:28])[CH:9]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 13819ChlorotriethylsilaneHCID 2733832Lithium HexamethyldisilazideHCID 57743258HCID 57743258, compound

Product 1

HCID 666412851-[5-Fluoro-2-(tetrahydro-pyran-4-yloxy)-phenyl]-3-trimethylsilyoxy-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-(tetrahydro-pyran-4-yloxy)-benzaldehyde was treated with LHMDS, acetyl chloride, triethylamine and chloro-triethyl-silane to give the desired compound, which was directly used for the next step.

Sources & evidence

ORD record
ord-39706d6b911a4fd499835bbb839d08ad
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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