Diethyl Malonate → Diethyl allylmalonate

HRID 717564Notes

Reaction equation

HRID 717564 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CC#N>[CH2:20]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 74900Diethyl allylmalonateYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 500 mL three necked round bottom flask was charged with diethyl malonate (20 g), dry potassium carbonate (43 g) and dry CH3CN (200 mL) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 10 minutes and allylbromide (23 g) was slowly added to the reaction mixture at room temperature. The reaction mixture was heated to 80° C. for 24 hours. The reaction mixture was cooled to room temperature and filtered through celite bed. The celite bed was washed with acetonitrile (100 mL) and the combined filtrate was concentrated to give diethyl 2-allylmalonate (24 g) as colorless liquid. 1H NMR (CDCl3): δ 1.26 (t, 6H), 2.61-2.67 (m, 2H), 3.42 (t, 1H), 4.20 (q, 4H), 5.03-5.16 (m, 2H), 5.70-5.85 (m, 1H).

Workup

  1. temperatureThe reaction mixture was heated to 80° C. for 24 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through celite bed
  4. washThe celite bed was washed with acetonitrile (100 mL)
  5. concentrationthe combined filtrate was concentrated

Sources & evidence

ORD record
ord-0984d193cff1437f83c099595aa78682
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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