Diethyl Malonate → HCID 56957354, compound

HRID 2170726Notes

Reaction equation

HRID 2170726 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br.[Cl-].[NH4+]>CS(C)=O>[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][C:2]([CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([Br:14])[CH:16]=1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 699793-Bromobenzyl bromide

Product 1

HCID 56957354HCID 56957354, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Diethyl malonate (4.53 mL, 30.0 mmol) was added gradually at 0° C. to a mixed liquid containing sodium hydride (55 wt % in oil, 2.95 g, 67.5 mmol) and anhydrous dimethylsulfoxide (60 mL). Following stirring of the resulting mixed liquid at this temperature for 30 minutes, 3-bromobenzyl bromide (15.7 g, 63.0 mmol) was added. The resulting mixed liquid was stirred at room temperature for 2 hours, and a saturated aqueous solution of ammonium chloride was then added to halt the reaction. The organic layer was separated from the mixed liquid, and the water layer was extracted with ethyl acetate. The thus obtained organic layer was washed with a saturated saline solution and then dried using anhydrous magnesium sulfate. The organic layer was then filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:1), yielding the title compound (4c) (12.7 g, 25.5 mmol) as a white solid in a yield of 85%.

Workup

  1. additionmixed liquid at this temperature for 30 minutes
  2. additionThe resulting mixed liquid
  3. stirringwas stirred at room temperature for 2 hours
  4. customthe reaction
  5. customThe organic layer was separated from the mixed liquid
  6. extractionthe water layer was extracted with ethyl acetate
  7. washThe thus obtained organic layer was washed with a saturated saline solution
  8. customdried
  9. filtrationThe organic layer was then filtered
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:1)

Sources & evidence

ORD record
ord-61927e1116c84bf380b837d8ff82183b
Source dataset
uspto-grants-2015_06
Patent number
US09051246B2

Reaction notes

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