Chlorotrimethylsilane → HCID 66597483, compound

HRID 1627769Notes

Reaction equation

HRID 1627769 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=O.[C:22]([O:29][CH3:30])(=[O:28])[CH2:23][CH2:24][C:25]([CH3:27])=O.Cl[Si](C)(C)C>CN(C=O)C>[CH3:27][C:25]1[N:1]=[C:2]2[S:3][CH:4]=[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]2=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[C:24]=1[CH2:23][C:22]([O:29][CH3:30])=[O:28]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 69354Methyl levulinateHCID 28337535HCID 28337535, compound

Product 1

HCID 66597483HCID 66597483, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure B from (2-amino-4-phenylthiophen-3-yl)(p-tolyl)methanone (0.264 g; 0.9 mmol), methyl levulinate (0.127 mL; 0.99 mmol), chlorotrimethylsilane (0.460 mL; 3.6 mmol) in DMF (3.6 mL) for 48 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (3-40%) in heptane furnished 0.297 g (85%) of the title compound as a yellow solid.

Workup

  1. customThis compound was prepared
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (3-40%) in heptane

Sources & evidence

ORD record
ord-7eb6fb38cd6d4e17ac57e2f3b144e527
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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