Magnesium → 1-[1-(p-Chlorophenyl)-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-2-butenyl]cyclopropane

HRID 1458395Notes

Reaction equation

HRID 1458395 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:27]2[CH2:29][CH2:28]2)=[C:9]([F:26])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)=[CH:4][CH:3]=1.[Mg]>CO.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:27]2[CH2:29][CH2:28]2)[C:9]([F:26])=[CH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 540353111-(p-Chlorophenyl)-1-cyclopropyl-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene

Product 1

HCID 544245031-[1-(p-Chlorophenyl)-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-2-butenyl]cyclopropaneYield 82%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 1-(p-chlorophenyl)-1-cyclopropyl-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene (26 g, 0.064 mol) in a methanol/tetrahydrofuran solution (15:1) is treated with magnesium turnings (7.72 g, 0.317 mol), stirred at room temperature for 4 hours, quenched with hydrochloric acid, and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 2N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and an ethyl acetate/hexanes solution (5:95) gives the title product as an oil (21.4 g, 82%) which is identified by NMR spectral analyses.

Workup

  1. customquenched with hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. washwashed sequentially with water, 2N hydrochloric acid and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-c419064b60524bfe964c9ead853558dc
Source dataset
uspto-grants-1998_12
Patent number
US05849958

Reaction notes

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