3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde → 3-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionaldehyde

HRID 1584336Notes

Reaction equation

HRID 1584336 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20])[CH:6]=[CH:7][CH:8]=[O:9]>[C].[Pd].O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][CH:8]=[O:9])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20]

Participants

4

Reactant 1

HCID 538228793-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde

Product 1

HCID 212244623-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionaldehyde

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamaldehyde (5.6 g), palladium-carbon (5%, 0.5 g) and tetrahydrofuran (THF) (160 ml) was subjected to catalytic hydrogenation at room temperature under 1 atmospheric pressure. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate -hexane (1:1), was obtained 3-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionaldehyde, which was recrystallized from ethyl acetate-hexane to give colorless needles, m.p.80-81° C.

Workup

  1. customwas subjected to catalytic hydrogenation at room temperature under 1 atmospheric pressure
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washFrom the fraction eluted with ethyl acetate -hexane (1:1)

Sources & evidence

ORD record
ord-19a3097309ed41babb10be80c4735499
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

Loading…