Ammonium Chloride → HCID 23071109, compound

HRID 1351970Notes

Reaction equation

HRID 1351970 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O)[CH3:2].[CH:18]([Mg]Br)=[CH2:19].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:7]=1[NH:12][CH:19]=[CH:18]2)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3386289HCID 3386289, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 23071109HCID 23071109, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

N,N-Diethyl-2-(2-nitrophenyl)acetamide (87.2 g, 0.369 mol) is dissolved in tetrahydrofuran (1.5L), and the mixture is cooled to −70° C. To the mixture is added dropwise a 1M solution of vinylmagnesium bromide in tetrahydrofuran (1.11 L, 1.11 mol). After the addition, the mixture is stirred at −50° C. for additional 5 hours. The reaction solution is poured into an aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The resulting residue is purified by silica gel column chromatography (chloroform, hexane/ethyl acetate=4/1) to give the title compound (4.02 g, yield: 5%).

Workup

  1. additionAfter the addition
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic layer is washed with a saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue is purified by silica gel column chromatography (chloroform, hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-65b3c379685749af84035dae8dc162eb
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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