Hydrochloric Acid → HCID 13707198, compound

HRID 1394057Notes

Reaction equation

HRID 1394057 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH:9](=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:10].Cl>CS(C)=O>[CH3:10][CH:9]1[CH2:2][C:11]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 73831Diethyl ethylidenemalonateHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

Product 1

HCID 13707198HCID 13707198, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 50.6 g of trimethylsulphoxonium iodide in 400 cm3 of dimethyl sulphoxide there are added, in one go, 8.84 g of 60% sodium hydride in oil. The reaction mixture is stirred for 2 hours and then a solution of 43.3 g of diethyl ethylidenemalonate in 200 cm3 of dimethyl sulphoxide is added dropwise over a period of 15 minutes. After stirring for 16 h, a mixture of ice and 100 cm3 of 1N hydrochloric acid is added and then the reaction mixture is extracted with ether (3×200 cm3). The combined organic phases are washed with sodium chloride solution and then dried over sodium sulphate and evaporated. Chromatography on silica gel (dichloromethane/cyclohexane: 75/25) allows 37.5 g of expected product to be isolated.

Workup

  1. stirringAfter stirring for 16 h
  2. additionis added
  3. extractionthe reaction mixture is extracted with ether (3×200 cm3)
  4. washThe combined organic phases are washed with sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customto be isolated

Sources & evidence

ORD record
ord-a19d9fc9fd764bd18435748e3ec35cc7
Source dataset
uspto-grants-2008_03
Patent number
US07348344B2

Reaction notes

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