HCID 10881778, compound → HCID 53888831, compound

HRID 233289Notes

Reaction equation

HRID 233289 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:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[CH2:23][OH:24])=[CH:17][CH:16]=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]=[CH:17][C:18]([CH:21]=[CH:22][CH:23]=[O:24])=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 10881778HCID 10881778, compound

Product 1

HCID 53888831HCID 53888831, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Activated manganese dioxide (MnO2) (9.0 g) was added to a solution of (E)-3-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]-2-propen-1-ol (3.7 g) in dichloromethane (80 ml), which was stirred for one hour at room temperature. The reaction mixture was subjected to filtration through celite layer. The filtrate was concentrated under reduced pressure to give 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamoaldehyde (2.6 g, 70%), which was recrystallized from ethyl acetate--hexane to yield colorless prisms, m.p.114°-115° C.

Workup

  1. filtrationThe reaction mixture was subjected to filtration through celite layer
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-df4db62a8c814d2abd8b132a2fa39efd
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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