Ammonium Chloride → HCID 23121503, compound

HRID 1631194Notes

Reaction equation

HRID 1631194 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[Mg][CH:21]=[CH2:22].[Cl-].[NH4+]>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH:15]([OH:16])[CH:21]=[CH2:22])=[CH:17][CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 211912554-(3-Phenylpropoxy)benzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 23121503HCID 23121503, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(3-phenylpropoxy)benzaldehyde (10.4 g) in dry tetrahydrofuran (100 mL), a solution of bromo(vinyl) magnesium in tetrahydrofuran (14%, about 1 M) was added at 0° C. After stirring for 15 minutes, the reaction mixture was added to a cold saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 3:1) to give the title compound (10.01 g) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1 to 3:1)

Sources & evidence

ORD record
ord-08e662704f5a4c368e7c54c521714012
Source dataset
uspto-grants-2014_07
Patent number
US08791159B2

Reaction notes

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