Toluene → HCID 131717970, compound

HRID 1587269Notes

Reaction equation

HRID 1587269 reaction equation
[C:1]1(C)C=C[CH:4]=[CH:3][CH:2]=1.[CH2:8]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([CH2:34][CH:35]=[CH2:36])=[O:33])=[CH:27][CH:26]=3)=[CH:23][N:24]=2)=[CH:16][CH:15]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:37]([SiH:41](C)[CH3:42])CCC>C(O)(C)C.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl.O>[CH2:8]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[S:21][C:22]([C:25]3[CH:26]=[CH:27][C:28]([O:31][C:32]([CH2:34][CH2:35][CH:36]([SiH:41]([CH3:42])[CH3:37])[CH2:1][CH2:2][CH2:3][CH3:4])=[O:33])=[CH:29][CH:30]=3)=[CH:23][N:24]=2)=[CH:18][CH:19]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 3

HCID 1140TolueneHCID 2757279Butyl(dimethyl)silaneHCID 19757574HCID 19757574, compound

Product 1

HCID 131717970HCID 131717970, compoundYield 24.3%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolCatalystHCID 61859Chloroplatinic acidCatalystHCID 962WaterSolvent

Procedure

2 ml of toluene was added to 0.81 g (1.99 mM) of 2-(4-hexylphenyl)-5-(4-allylcarbonyloxyphenyl)-1,3-thiazole, followed by stirring at room temperature. To the mixture, an appropriate amount chloroplatinic acid, three drops of isopropyl alcohol and 0.24 g (2.06 mM) of butyldimethylsilane were successively added and heated to 80° C., followed by stirring for 7 hours. After the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with water and dried with anhydrous magnesium sulfate. The magnesium sulfate in the resultant organic layer was filtered off, followed by distilling-off of the solvent, purification by silica gel column chromatography (eluent: toluene) and recrystallization from a mixture solvent (methanol/toluene) to obtain 0.25 g of 2-(4-hexylphenyl)-5-[4-(3-butyldimethylsilylpropylcarbonyloxy)phenyl]-1,3-thiazole (Yield: 24.3%). ##STR83##

Workup

  1. temperatureheated to 80° C.
  2. stirringby stirring for 7 hours
  3. customAfter the reaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationThe magnesium sulfate in the resultant organic layer was filtered off
  8. distillationfollowed by distilling-off of the solvent, purification by silica gel column chromatography (eluent: toluene) and recrystallization from a mixture solvent (methanol/toluene)

Sources & evidence

ORD record
ord-eb030b85cbf9487bac79abb6c7d2bef6
Source dataset
uspto-grants-1993_06
Patent number
US05217645

Reaction notes

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