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

HRID 1739044
Notes
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Reaction equation

HRID 1739044 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].C1CCN2C(=NCCC2)CC1.Cl>C1(C)C=CC=CC=1>[CH3:6][O:5][C:3](=[O:4])[CH:2]=[CH: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:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])=[C:10]([F:28])[CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
85 °C

Procedure

A mixture of methyl 2-bromo-3-[3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]propionate (14.2 g), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) (4.83 g) and toluene (150 ml) was stirred at 80 to 90° C. for 2 hours, and then poured into 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give methyl3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)-cinnamate (10.0 g, 86%). This product was recrystallized from dichloromethane-methanol. Colorless prisms, mp: 167-168° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-517f058724e54185a5c961abad8528ab
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05965589

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes