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

HRID 1095192

Reaction equation

HRID 1095192 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:16][CH2:15][S: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].[CH3:31][SiH:32]([CH3:34])[CH3:33]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:16][CH2:15][S:14][CH2:13][CH2:12]2)=[C:6]([CH:7]=[N:22][C:27]([O:29][Si:32]([CH3:34])([CH3:33])[CH3:31])=[CH2:28])[CH:9]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 70435TrimethylsilaneHCID 2733832Lithium HexamethyldisilazideHCID 577432645-Chloro-2-(tetrahydro-thiopyran-4-yloxy)-benzaldehyde

Product 1

HCID 666407541-[5-Chloro-2-(tetrahydro-thiopyran-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-chloro-2-(tetrahydro-thiopyran-4-yloxy)-benzaldehyde was treated with LHMDS, acetyl chloride, triethylamine and trimethyl silane to give the desired compound, which was directly used for the next step.

Sources & evidence

ORD record
ord-df035aa4fb3343b69c7cbf33d7cdd5b6
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Linked notes

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