Methyl iodide → Methyl 5-oxohexanoate

HRID 1650251Notes

Reaction equation

HRID 1650251 reaction equation
[C:1](=O)(O)[O-].[Na+].[C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:8])[CH3:7].CI>CN(C)C=O.O>[C:6]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:1])=[O:13])(=[O:8])[CH3:7]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 184074-Acetylbutyric acidHCID 516892Sodium Bicarbonate

Product 1

HCID 84129Methyl 5-oxohexanoateYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a rapidly stirred slurry of sodium bicarbonate (25 g) in a solution of 4-acetylbutyric acid (13 g, 0.1 mol) in dimethylformamide (150 ml) was added methyl iodide (47 g). After stirring overnight at room temperature under nitrogen, the reaction mixture was diluted with water (300 ml) and extracted with ethyl ether (250 ml). The organic phase was washed with water and dried over sodium sulfate. The drying agent was filtered and the filtrate concentrated on the rotary evaporator to give 12 g of the title compound as a light yellow oil. The product can be purified by distillation: b.p. 59°-60° (0.1 mm Hg).

Workup

  1. extractionextracted with ethyl ether (250 ml)
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe drying agent was filtered
  5. concentrationthe filtrate concentrated on the rotary evaporator

Sources & evidence

ORD record
ord-b3da2083dc6147d1a6cfe78c819acc20
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

Loading…