Ammonium Chloride → HCID 67777834, compound

HRID 1026292Notes

Reaction equation

HRID 1026292 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)[CH:5]=[CH:4][C:3]=1[CH2:13][C:14](N(OC)C)=[O:15].[CH3:20][Mg]Br.C1(C)C=CC=CC=1.C(OCC)C.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:11][CH2:12]2)[CH:5]=[CH:4][C:3]=1[CH2:13][C:14](=[O:15])[CH3:20]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 22238780Ether tolueneHCID 86666272HCID 86666272, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67777834HCID 67777834, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (50 mL) of 2-[2-bromo-4-(cyclopropylmethoxy)phenyl]-N-methoxy-N-methylacetamide (3.00 g) in THF was added dropwise methylmagnesium bromide (19.6 mL, 1.4 M, a mixed solution of toluene-diethyl ether (3/1)) under ice-cooling. The mixture was stirred at room temperature for 3 hr, poured into saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a colorless oil (1.29 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated 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 (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ce42472e7f4042cd84140557cfc1a4d9
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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