HCID 117600653, compound → HCID 117600516, compound

HRID 1496991Notes

Reaction equation

HRID 1496991 reaction equation
[CH2:1]([O:3][C:4](=[O:24])/[CH:5]=[C:6](/[C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Br:23])[CH:14]=1)\[C:7]1[O:8][C:9]([CH3:12])=[N:10][N:11]=1)[CH3:2]>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]([C:13]1[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:16]=[C:15]([Br:23])[CH:14]=1)[C:7]1[O:8][C:9]([CH3:12])=[N:10][N:11]=1)[CH3:2]

Participants

4

Reactant 1

HCID 117600653HCID 117600653, compound

Product 1

HCID 117600516HCID 117600516, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Procedure

11.2 g (27.64 mmol) (Z)-3-(3-Bromo-5-trifluoromethyl-phenyl)-3-(5-methyl-[1,3,4]oxadiazol-2-yl)-acrylic acid ethyl ester is dissolved in 200 ml acetic acid and 14.1 g Zinc dust (215.6 mmol, 7.8 mmol) 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. 3.97 g of 3-(3-Bromo-5-trifluoromethyl-phenyl)-3-(5-methyl-[1,3,4]oxadiazol-2-yl)-propionic acid ethyl ester (yield=35%) are isolated.

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-3382bca28c52483194ba03287cb39736
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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