Ammonium Chloride → HCID 66975384, compound

HRID 1022596Notes

Reaction equation

HRID 1022596 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][CH:5](/[CH:7]=[CH:8]/[N+:9]([O-:11])=[O:10])[CH2:4][O:3]1.Br[Mg][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1.[Cl-].[NH4+]>C1COCC1>[Cl:21][C:18]1[CH:19]=[C:20]([CH:7]([CH:5]2[CH2:4][O:3][C:2]([CH3:12])([CH3:1])[O:6]2)[CH2:8][N+:9]([O-:11])=[O:10])[CH:15]=[CH:16][C:17]=1[Cl:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 66975281HCID 66975281, compoundHCID 178478192HCID 178478192, compound

Product 1

HCID 66975384HCID 66975384, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (E)-2,2-dimethyl-4-(2-nitrovinyl)-1,3-dioxolane (22.29 g) synthesized according to the method described in Tetrahedron Letters, 36 (25), 4447-4450 (1995) in THF (200 ml) was added 1 M THF solution (193 mL) of bromo(3,4-dichlorophenyl)magnesium in an inert atmosphere at −78° C. The reaction mixture was stirred at room temperature for 2 hr, and added to aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (12.16 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1f04068a361440efb79960cdcdd18e47
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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