Diethyl Ether → HCID 67958514, compound

HRID 527658Notes

Reaction equation

HRID 527658 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10](=[O:12])[CH3:11].[CH3:13][Mg]Br.CCOCC>C1COCC1>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]([OH:12])([CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 106786141-(2-Amino-6-methoxyphenyl)ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 67958514HCID 67958514, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(2-Amino-6-methoxyphenyl)ethanone (500 mg, 3.03 mmol) was dissolved in THF (7.5 mL) and cooled to 0° C. A 3M solution of Methyl magnesium bromide in Et2O (2.12 ml, 6.36 mmol) was added drop wise keeping the temperature below 10° C. The reaction was quenched with an aqueous saturated solution of NH4Cl (7.5 mL) keeping the temperature below 15° C. The mixture was diluted with water and ethyl acetate, two phases separated and the organic layer was washed twice with brine, dried over Na2SO4 and evaporated to dryness affording the title compound (500 mg) as light orange solid.

Workup

  1. customthe temperature below 10° C
  2. customThe reaction was quenched with an aqueous saturated solution of NH4Cl (7.5 mL)
  3. customthe temperature below 15° C
  4. additionThe mixture was diluted with water and ethyl acetate, two phases
  5. customseparated
  6. washthe organic layer was washed twice with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-2649a1e0b7f742a4a1934da9c09a57b6
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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