Hydrochloric Acid → Methyl 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate

HRID 1584345Notes

Reaction equation

HRID 1584345 reaction equation
Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[C:10]([F:28])[CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].N12CCCN=C1CCCCC2.Cl>C1(C)C=CC=CC=1>[F:28][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:19][C:20]=1[CH3:21])[CH:7]=[CH:2][C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10983188Methyl 2-bromo-3-[3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionate

Product 1

HCID 54362890Methyl 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamateYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-bromo-3-[3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionate (14.1 g), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (4.8 g) and toluene (150 ml) was stirred for 2 hours at temperatures ranging from 80 to 90° C. The reaction mixture was poured into 2N HCl, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), followed by distilling off the solvent under reduced pressure to yield methyl 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)cinnamate (10.0 g). The product was recrystallized from dichloromethane-methanol to give colorless prisms, m.p.167-168° C.

Workup

  1. customranging from 80 to 90° C
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-a099c05d68434ed7acf0a24e2d4b7121
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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