Sodium Iodide → HCID 67786251, compound

HRID 1756762Notes

Reaction equation

HRID 1756762 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].CS(O[CH2:19][CH:20]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]2[O:32][CH2:33][O:34][C:27]=12)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=O)=O.[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[CH2:12]([O:11][C:3](=[O:10])[CH:4]([CH2:19][CH:20]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]2[O:32][CH2:33][O:34][C:27]=12)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 54536594HCID 54536594, compound

Product 1

HCID 67786251HCID 67786251, compoundYield 39.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 0.40 g of sodium hydride (60% oil dispersion, 10 mmol) in 10 ml of N,N-dimethylformamide was dropwise added 1.60 g (10 mmol) of diethyl malonate under ice cooling, and the resultant mixture was stirred for 30 minutes. To this mixture were added a solution of 3.14 g (10 mmol) of 2-(2, 3-methylenedioxyphenyl)heptyl methanesulfonate, intermediate in Reference Example 1. in 6 ml of N,N-dimethylformamide and 1.50 g (10 mmol) of sodium iodide, and the mixture was stirred at 100° C. for 2 hours. After cooling, the mixture was mixed with water and shaken with ethyl acetate. The extract was washed with saturated saline, dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo. The residue was chromatographed on a column of silica gel, eluting with ethyl acetate/hexane (1/10) to give 1.49 g of 2-(2, 3-methylenedioxyphenyl)heptylmalonic acid diethyl ester as an oil.

Workup

  1. temperatureAfter cooling
  2. washThe extract was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was chromatographed on a column of silica gel
  6. washeluting with ethyl acetate/hexane (1/10)

Sources & evidence

ORD record
ord-78cd3f47e5f94b03b2943f48c0e76108
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

Loading…