1,4-Dioxane → HCID 19965610, compound

HRID 977251Notes

Reaction equation

HRID 977251 reaction equation
[CH3:1][C:2]1[S:6][C:5](/[CH:7]=[CH:8]/[C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:4][C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O1CCOCC1>[C].[Pd].CO>[CH3:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[N:4][C:3]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 86750602HCID 86750602, compound

Product 1

HCID 19965610HCID 19965610, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl (E)-4-[2-(5-methyl-4-phenyl-2-thiazolyl)vinyl]benzoate (9.5 g), palladium-carbon (5%, 1.0 g) and dioxane (70 ml)-methanol (60 ml) was subjected to catalytic hydrogenation at 1 atm and room temperature. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure to yield methyl 4-[2-(5-methyl-4-phenyl-2thiazolyl)ethyl]benzoate (9.0 g, 94%), which was then recrystallized from hexane to yield colorless plates having a melting point of 52°-53° C.

Workup

  1. customwas subjected to catalytic hydrogenation at 1 atm and room temperature
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-54aa81714629448dac1b04abbccbe44b
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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