Ammonium Chloride → HCID 67777995, compound

HRID 1026353Notes

Reaction equation

HRID 1026353 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][C:13](N(OC)C)=[O:14].[CH3:19][Mg]Br.[Cl-].[NH4+]>CCOCC>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][C:13](=[O:14])[CH3:19]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86666325HCID 86666325, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67777995HCID 67777995, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-(2-bromo-4-(methoxymethoxy)phenyl)-N-methoxy-N-methylacetamide (4.30 g) in ether (93 ml) was added methyl magnesium bromide (3 M in ether, 63 mL) dropwise at 0° C. After addition, the solution was stirred at 0° C. for 1.5 hr. The mixture was poured into saturated aqueous ammonium chloride, and extracted with ethyl acetate (100 mL×2). The organic phase was dried over anhydrous sodium sulfate, The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to afford the title compound (23 g).

Workup

  1. additionAfter addition
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-37997edc57b14f64a5ef7edca2b299d7
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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