Magnesium → 4-(3-[1,3]Dioxan-2-ylphenyl)-1,1,1-trifluoro-4-methylpentan-2-one

HRID 400622Notes

Reaction equation

HRID 400622 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[Mg].[F:15][C:16]([F:24])([F:23])[C:17](=[O:22])[CH:18]=[C:19]([CH3:21])[CH3:20]>C1COCC1.[Cu]I>[O:9]1[CH2:10][CH2:11][CH2:12][O:13][CH:8]1[C:4]1[CH:3]=[C:2]([C:19]([CH3:21])([CH3:20])[CH2:18][C:17](=[O:22])[C:16]([F:24])([F:23])[F:15])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 5462224MagnesiumHCID 101058152-(3-Bromophenyl)-1,3-dioxaneHCID 220326911,1,1-Trifluoro-4-methylpent-3-en-2-one

Product 1

HCID 578099664-(3-[1,3]Dioxan-2-ylphenyl)-1,1,1-trifluoro-4-methylpentan-2-one

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the Grignard reagent (generated from the reaction of 2-(3-bromophenyl)-[1,3]dioxane with magnesium turnings in THF, 0.25 M, 52.6 mL, 13.1 mmol) was treated with copper (I) iodide (2.5 g, 13.1 mmol) at 0° C. After 45 minutes, 1,1,1-trifluoro-4-methylpent-3-en-2-one (2 g, 13.1 mmol) was added, and the reaction mixture was slowly warmed to room temperature and stirred overnight. The mixture was quenched with aqueous saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with aqueous saturated sodium chloride solution, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was triturated with hexanes and filtered. The filtrate was concentrated in vacuo to give 1.78 g of the crude product, which was used without purification.

Workup

  1. customThe mixture was quenched with aqueous saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with aqueous saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with hexanes
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ec425f3f3bb04310aa0e9e7d7f3014dc
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

Loading…