Methyl iodide → Methyl 4-oxohexanoate

HRID 1646889Notes

Reaction equation

HRID 1646889 reaction equation
[C:1]([O-])([O-])=O.[Cs+].[Cs+].[O:7]=[C:8]([CH2:14][CH3:15])[CH2:9][CH2:10][C:11]([OH:13])=[O:12].IC.CCOC(C)=O>CN(C=O)C.O>[O:7]=[C:8]([CH2:14][CH3:15])[CH2:9][CH2:10][C:11]([O:13][CH3:1])=[O:12]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 37997744-Oxohexanoic acid

Product 1

HCID 546293Methyl 4-oxohexanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of 8.15 g (25 mmol) of Cs2CO3 in DMF was added 5.79 g (44 mmol) of 4-oxohexanoic acid. After 5 minutes, 6.81 g (48 mmol) of iodomethane was added. The reaction mixture was stirred at ambient temperature for 16 hours. To the reaction was then added 250 mL of EtOAc and 250 mL of H2O. The layers were separated, and the organic layer was washed with 3×250 mL of H2O. The organic layer was then dried over Na2SO4 anhydrous, filtered, and concentrated under vacuum. The yield of methyl 4-oxohexanoate (16) was 4.15 g (65%), which was employed in Example 17 below.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with 3×250 mL of H2O
  3. dry with materialThe organic layer was then dried over Na2SO4 anhydrous
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b451ba1a5e444327a7d0889c6abf9365
Source dataset
uspto-grants-1993_01
Patent number
US05182272

Reaction notes

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