Diethyl Malonate → Diethyl p-isopropylbenzylmalonate

HRID 2164431Notes

Reaction equation

HRID 2164431 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+].[H][H].[CH:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1)([CH3:18])[CH3:17]>CS(C)=O>[CH:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:21][CH:20]=1)([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 477191-(Bromomethyl)-4-(propan-2-yl)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 13178369Diethyl p-isopropylbenzylmalonate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Diethyl malonate was added dropwise at 20°-25° C. to a stirred suspension of sodium hydride (1 equi) in dry DMSO. The mixture was stirred until the evolution of hydrogen had ceased (ca. 1 hour), then a solution of p-isopropylbenzyl bromide (1 equiv.) (prepared from p-isopropylbenzyl alcohol and PBr3) in dry DMSO added dropwise with stirring. After stirring at room temperature for 1.5 hours the mixture was heated on the steam bath for 0.5 hour until a clear solution was obtained. The mixture was poured onto ice, extracted several times with ether and the extracts combined and washed with water and brine, dried (MgSO4) and evaporated in vacuo. The residual oil was distilled, collecting the fraction b.p. 160°-170° (2-3 mm).

Workup

  1. custom(ca. 1 hour)
  2. stirringAfter stirring at room temperature for 1.5 hours the mixture
  3. temperaturewas heated on the steam bath for 0.5 hour until a clear solution
  4. customwas obtained
  5. additionThe mixture was poured onto ice
  6. extractionextracted several times with ether
  7. washwashed with water and brine
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo
  10. distillationThe residual oil was distilled
  11. customcollecting the fraction b.p. 160°-170° (2-3 mm)

Sources & evidence

ORD record
ord-5b6a3658102348cfaecbc90eefea3c8f
Source dataset
uspto-grants-1985_03
Patent number
US04504492

Reaction notes

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