methyl (E)-2-bromomethyl-beta-methoxycinnamate → methyl (E)-beta-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamate

HRID 1735702Notes

Reaction equation

HRID 1735702 reaction equation
[OH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH3:13][O:14]/[C:15](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Br)=[CH:16]/[C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C.C(=O)([O-])[O-].[Ag+2]>[CH3:13][O:14]/[C:15](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][O:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1)=[CH:16]/[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 2

HCID 11219857methyl (E)-2-bromomethyl-beta-methoxycinnamateHCID 178517449HCID 178517449, compound

Product 1

HCID 86749648methyl (E)-beta-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamateYield 56.2%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

1.2 g (0.007 mol) of 2-hydroxy-4-phenylthiazole, 2.1 g (0.0077 mol) of silver carbonate and 2.1 g (0.0074 mol) of methyl (E)-β-methoxy-2-bromomethylcinnamate (see Example 2) are stirred in 15 ml of DMF at 60° C. for 8 hours. The precipitate is filtered off and the DMF solution is poured into 100 ml of water, and the mixture is extracted with methyl tert-butyl ether. Drying and concentration of the organic phase result in a brown oil which is chromatographed on silica gel with cyclohexane/acetone (95:5). 1.5 g (56% yield) of methyl (E)-β-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamate as yellowish oil are isolated as the main fraction.

Workup

  1. filtrationThe precipitate is filtered off
  2. additionthe DMF solution is poured into 100 ml of water
  3. extractionthe mixture is extracted with methyl tert-butyl ether
  4. customDrying
  5. customconcentration of the organic phase result in a brown oil which
  6. customis chromatographed on silica gel with cyclohexane/acetone (95:5)

Sources & evidence

ORD record
ord-eafe3c5976c948ffad0f0ea1f2942595
Source dataset
uspto-grants-1996_07
Patent number
US05538940

Reaction notes

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