Sodium Iodide → HCID 14882717, compound

HRID 1461742Notes

Reaction equation

HRID 1461742 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[I-].[Na+].Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([CH2:23][C:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[O:25])[CH2:18]1>O1CCCC1>[C:3]([CH:2]([CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([CH2:23][C:24]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)=[O:25])[CH2:18]1)[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 14882716HCID 14882716, compound

Product 1

HCID 14882717HCID 14882717, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.2 g of ethyl acetoacetate is added at 0° C. to a suspension of 1.13 g of sodium hydride in 150 ml of tetrahydrofuran. After 15 minutes at this temperature, 7.1 g of anhydrous sodium iodide are added, followed by the addition at 0° C. of l3.5g of the product obtained in Stage B. The mixture is then brought to reflux for 12 hours and the whole is thereafter concentrated, the residue is taken up in water and the product is extracted with dichloromethane. The 16.9 g of oil obtained are purified by chromatography on 900 g of silica (70-230 mesh), using a mixture of dichloromethane and methanol (98:2 V/V) as eluant.

Workup

  1. temperatureto reflux for 12 hours
  2. concentrationthe whole is thereafter concentrated
  3. extractionthe product is extracted with dichloromethane

Sources & evidence

ORD record
ord-7b83243da2a146179b3e7cda389f8e3c
Source dataset
uspto-grants-1991_12
Patent number
US05077288

Reaction notes

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