Methyl iodide → Methyl 2-methyl-3-oxopentanoate

HRID 2401205Notes

Reaction equation

HRID 2401205 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:10](=O)([O-])[O-].[K+].[K+].IC>O1CCCC1>[CH3:10][CH:3]([C:2](=[O:1])[CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Conditions

Temperature
0 °C

Procedure

Methyl 3-oxopentanoate (6.27 ml, 50 mmol) in tetrahydrofuran (100 ml) and potassium carbonate (20.73 g, 150 mmol) was heated at reflux under argon for 3 hours, reaction mixture was cooled in an ice bath and and iodomethane (3.75 ml, 60.0 mmol) was added dropwsie. The reaction mixture was stirred at 0° C. for 6 hours, and allowed to warm to room temperature while stirring overnight. The reaction mixture was filtered through a celite and the filtrate was evaporated under reduced pressure to give the title compound as an oil (7.2 g);

Workup

  1. temperatureat reflux under argon for 3 hours
  2. customreaction mixture
  3. temperaturewas cooled in an ice bath
  4. temperatureto warm to room temperature
  5. stirringwhile stirring overnight
  6. filtrationThe reaction mixture was filtered through a celite
  7. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8b7c606500d1481c89270802f8f8ae1b
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

Loading…