Dimethylformamide → Methyl 5-oxohexanoate

HRID 917402

Reaction equation

HRID 917402 reaction equation
CN(C)[CH:3]=[O:4].[O:6]=[C:7]([CH3:14])[CH2:8][CH2:9][CH2:10][C:11](O)=[O:12].C(=O)([O-])[O-].[K+].[K+].CI>O>[O:6]=[C:7]([CH3:14])[CH2:8][CH2:9][CH2:10][C:11]([O:4][CH3:3])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 184074-Acetylbutyric acid

Product 1

HCID 84129Methyl 5-oxohexanoateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 80 ml of N,N-dimethylformamide, 25 g (0.19 mol) of 5-oxohexanoic acid and 43 g (0.31 mol) of potassium carbonate were dissolved and heated at 50° C., followed by drop-wisely adding 41 g (0.29 mol) of methyl iodide and stirring at the same temperature for 2 hours. To this mixture, 150 ml of water was added, followed by extracting with diethyl ether (200 ml×4). The organic layer was washed with a saturated saline solution, followed by drying over anhydrous magnesium sulfate and concentrating under reduced pressure to obtain 24.9 g (yield: 90%) of methyl 5-oxohexanoate.

Workup

  1. extractionby extracting with diethyl ether (200 ml×4)
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-bad5e512292141079f15f63ff88e8288
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Linked notes

Loading…