(E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propenol → 3-(5-Methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde

HRID 1739035Notes

Reaction equation

HRID 1739035 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][O:14][C:15]1[CH:16]=[C:17](/[CH:21]=[CH:22]/[CH2:23][OH:24])[CH:18]=[CH:19][CH:20]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[CH:21]=[CH:22][CH:23]=[O:24]

Participants

4

Reactant 1

HCID 10860209(E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propenol

Product 1

HCID 542788533-(5-Methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehydeYield 96.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Activated manganese dioxide (25.0 g) was added to a solution of (E)-3-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-phenyl]-2-propenol (11.0 g) in dichloromethane (200 ml), and the mixture was stirred at room temperature for 2 hours. The insoluble materials were filtered off, and the filtrate was concentrated under reduced pressure to give 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde (10.5 g, 96%). This product was recrystallized from ethyl acetate-hexane. Colorless columns, mp: 103-104° C.

Workup

  1. filtrationThe insoluble materials were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-917e47271b14424bbf4ec408422eee6f
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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