HCID 117600636, compound → HCID 117600518, compound

HRID 1746468Notes

Reaction equation

HRID 1746468 reaction equation
[CH2:1]([O:3][C:4](=[O:20])/[CH:5]=[C:6](/[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([Br:19])[CH:13]=1)\[C:7]1[O:8][CH:9]=[CH:10][N:11]=1)[CH3:2]>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([Br:19])[CH:13]=1)[C:7]1[O:8][CH:9]=[CH:10][N:11]=1)[CH3:2]

Participants

4

Reactant 1

HCID 117600636HCID 117600636, compound

Product 1

HCID 117600518HCID 117600518, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

9.5 g (27.93 mmol) (Z)-3-(3-Bromo-5-fluoro-phenyl)-3-oxazol-2-yl-acrylic acid ethyl ester is dissolved in 200 ml acetic acid and 9.5 g Zinc dust (11 Ea)) is added slowly over a period of 30 minutes. The temperature of the reaction mixture is not allowed to reach >30° C. during the addition of the zinc dust. The resulting mixture is allowed to stir overnight. After filtration 200 ml EtOAc and 200 ml water are added and the organic phase is separated and washed with brine. After removal of the solvent the crude material is purified by column chromatography on silica gel using heptane/EtOAc=3:1 as eluent. 9.50 g of 3-(3-Bromo-5-fluoro-phenyl)-3-oxazol-2-yl-propionic acid ethyl ester are isolated (yield=615)

Workup

  1. filtrationAfter filtration 200 ml EtOAc and 200 ml water
  2. additionare added
  3. customthe organic phase is separated
  4. washwashed with brine
  5. customAfter removal of the solvent the crude material
  6. customis purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-fdb000e5007247ab9ee77fd391b83944
Source dataset
uspto-grants-2015_10
Patent number
US09150526B2

Reaction notes

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