HCID 19965653, compound → HCID 86750600, compound

HRID 977258Notes

Reaction equation

HRID 977258 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH2:27][OH:28])=[CH:21][CH:20]=1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH:17]=[CH:18][C:19]1[CH:20]=[CH:21][C:22](/[CH:25]=[CH:26]/[CH:27]=[O:28])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 19965653HCID 19965653, compound

Product 1

HCID 86750600HCID 86750600, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of (E,E)-3-[4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]phenyl]-2-propenol (2.80 g), activated manganese dioxide (8.40 g) and chloroform (150 ml) was stirred at room temperature for 16 hours. After the manganese dioxide was filtered off, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to yield (E)-4-[2-[5-methyl-2-(2-naphthyl)-4-oxazolyl]vinyl]cinnamaldehyde (2.50 g, 90%) from the fraction eluted with chloroform, which was then recrystallized from dichloromethane-methanol to yield light yellow prisms having a melting point of 213°-214° C.

Workup

  1. filtrationAfter the manganese dioxide was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-843b66061e1947e9b1b13afec5a29f5c
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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