Ammonium Chloride → HCID 23121503, compound

HRID 1169633Notes

Reaction equation

HRID 1169633 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-d4f6c74520a94640819d9dd63679654d
Source dataset
uspto-grants-2010_11
Patent number
US07825109B2

Reaction notes

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