Chlorotrimethylsilane → HCID 66597209, compound

HRID 1627760Notes

Reaction equation

HRID 1627760 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=O.[CH3:19][O:20][C:21](=[O:32])[CH2:22][CH2:23][C:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl[Si](C)(C)C>CN(C=O)C>[C:25]1([C:24]2[N:1]=[C:2]3[S:6][C:5]4[CH2:7][CH2:8][CH2:9][C:4]=4[C:3]3=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[C:23]=2[CH2:22][C:21]([O:20][CH3:19])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 141190Benzenebutanoic acid, gamma-oxo-, methyl esterHCID 860207436093-41-3

Product 1

HCID 66597209HCID 66597209, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure B from (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-p-tolylmethanone (0.257 g; 1 mmol), methyl-3-benzoylpropionate (0.211 g; 1.1 mmol), chlorotrimethylsilane (0.526 mL; 4 mmol) in DMF (4 mL) for 18 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-50%) in heptane furnished 0.198 g (48%) of the title compound as a yellow oil.

Workup

  1. customThis compound was prepared
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (5-50%) in heptane

Sources & evidence

ORD record
ord-b5f8636ff6d14a21b835bd46ad149aa4
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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