HCID 117600729, compound → HCID 117600281, compound

HRID 1746461Notes

Reaction equation

HRID 1746461 reaction equation
[CH2:1]([O:3][C:4](=[O:21])/[CH:5]=[C:6](/[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Br:20])[CH:14]=1)\[C:7]1[S:8][C:9]([CH3:12])=[CH:10][N:11]=1)[CH3:2]>C(OCC)C.CC(O)=O.CCOC(C)=O.[Zn]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Br:20])[CH:14]=1)[C:7]1[S:8][C:9]([CH3:12])=[CH:10][N:11]=1)[CH3:2]

Participants

6

Reactant 1

HCID 117600729HCID 117600729, compound

Product 1

HCID 117600281HCID 117600281, compoundYield 99%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

18 g (46.55 mmol) of (Z)-3-(3-Bromo-5-chloro-phenyl)-3-(5-methyl-thiazol-2-yl)-acrylic acid ethyl ester are dissolved in 250 ml Diethylether and 80 ml AcOH. 3 Eq (140 mmol) of zinc dust are added over a period of 60 minutes. The resulting mixture is allowed to stir overnight, diluted with 100 ml EtOAc and filtrated over a pad of Celite. The solvent is removed in vacuo, the residue taken up in EtOAc, washed with brine and dried over MgSO4. After evaporation of the solvent 17 g (Yield=99%) of crude product are obtained, which are used in the last step.

Workup

  1. filtrationfiltrated over a pad of Celite
  2. customThe solvent is removed in vacuo
  3. washwashed with brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-f561e24452ef48759925ed57e12eeda8
Source dataset
uspto-grants-2015_10
Patent number
US09150526B2

Reaction notes

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