Dimethyl Sulfoxide → HCID 20066209, compound

HRID 551652Notes

Reaction equation

HRID 551652 reaction equation
[Cl-].[Li+].CS(C)=O.[CH2:7]([C:10]([CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)(C(OCC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH2:9]>O>[CH:21]1([CH:10]([CH2:7][CH:8]=[CH2:9])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 433294Lithium ChlorideHCID 67198959HCID 67198959, compound

Product 1

HCID 20066209HCID 20066209, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
185 °C

Procedure

Lithium chloride (3.60 g, 84.9 mmol) and water (0.76 mL, 41.9 mmol) were added to a dimethyl sulfoxide (20 mL) solution of diethyl allyl(cyclopentyl)malonate (10.10 g, 37.7 mmol), and the mixture was stirred at 185° C. for 6 hours. The mixture was treated with water, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain the compound of interest as a brown oil substance (6.10 g, 84%).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. customto obtain the compound of interest as a brown oil substance (6.10 g, 84%)

Sources & evidence

ORD record
ord-3d32a77e9ddc46c093ee2604bc3ad74f
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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