Acetone → HCID 19764540, compound

HRID 248074Notes

Reaction equation

HRID 248074 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[I-].[K+].BrCC(O[C:26]([CH3:29])([CH3:28])[CH3:27])=O.[CH3:30]C(C)=O>>[C:26]([CH2:29][C:13]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)=[O:16])([CH3:30])([CH3:28])[CH3:27]

Participants

6

Reactant 5

HCID 180AcetoneHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 2761030Methyl 2-(4-aminophenyl)acetate

Product 1

HCID 19764540HCID 19764540, compound

Procedure

Dissolve methyl (4-aminophenyl)acetate (14.9 g, 90.3 mmol) in acetone (300 mL). Add potassium carbonate (13.7 g, 99.3 mmol), potassium iodide (1.47 g, 9.03 mmol) and t-butyl bromoacetate (16 mL, 99.3 mmol). Heat at reflux for 20 hours then remove 200 mL of acetone in vacuo. Dilute the residue with ethyl ether (500 mL), wash with water (2×300 mL) and brine (300 mL). Dry (MgSO4) and evaporate the solvent in vacuo. Purify by flash chromatography to give the title compound.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 20 hours
  3. customthen remove 200 mL of acetone in vacuo
  4. additionDilute the residue with ethyl ether (500 mL)
  5. washwash with water (2×300 mL) and brine (300 mL)
  6. dry with materialDry (MgSO4)
  7. customevaporate the solvent in vacuo
  8. customPurify by flash chromatography

Sources & evidence

ORD record
ord-36908176080c4c6aa016a674de5da606
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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