(Z)-2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2-propenyl]-1,3-dioxane → 2-[3-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl]-1,3-dioxane

HRID 1377655

Reaction equation

HRID 1377655 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]\[CH2:24][CH:25]2[O:30][CH2:29][CH2:28][CH2:27][O:26]2)=[CH:18][CH:17]=1>[C].[Pd].C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][CH2:24][CH:25]2[O:30][CH2:29][CH2:28][CH2:27][O:26]2)=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 11811571(Z)-2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2-propenyl]-1,3-dioxane

Product 1

HCID 110259022-[3-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl]-1,3-dioxaneYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of (Z)-2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]-2-propenyl]-1,3-dioxane (5.0 g), palladium-carbon (5%, 0.1 g) and ethanol (100 ml) was subjected to catalytic hydrogenation at room 5 temperature under one atmospheric pressure. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography. From the fractions eluted with hexane--ethyl acetate (1:1), 2-[3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propyl]-1,3-dioxane (4.8 g, 96%) was obtained.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe concentrate was purified by means of a silica gel column chromatography
  4. washFrom the fractions eluted with hexane--ethyl acetate (1:1)

Sources & evidence

ORD record
ord-b6bf045aeb2148a1b4b3c030cdc2e274
Source dataset
uspto-grants-1997_09
Patent number
US05665748

Linked notes

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