Methyl cyanoacetate → HCID 13632645, compound

HRID 280387Notes

Reaction equation

HRID 280387 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]([CH3:20])=[CH:17][CH2:18]Br>O1CCCC1>[C:1]([C:3]1([C:4]([O:6][CH3:7])=[O:5])[CH2:18][CH:17]1[C:16]([CH3:20])=[CH2:15])#[N:2]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 11430Potassium CarbonateHCID 20585818860-95-2

Product 1

HCID 13632645HCID 13632645, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 65.3 g of methyl cyanoacetate, 228 g of freshly pulverized potassium carbonate and 800 ml of anhydrous tetrahydrofuran was heated at reflux under nitrogen for 2 hours. A solution of 150.5 g of 1,4-dibromo-2-methyl-2-butene in 500 ml of anhydrous tetrahydrofuran was added slowly dropwise to the refluxing reaction mixture over a period of two days. The solids were removed from the cooled reaction mixture by filtration through a bed of celite. The filtrate was concentrated in vacuo to leave 111.4 g of yellow oil. Distillation of the oil gave 81.3 g of the desired product as a colorless oil: b.p. 95°-105° C. (0.05 mm Hg) consisting of two isomers in a ratio of 2:1 by GLC.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 2 hours
  3. customThe solids were removed from the cooled reaction mixture by filtration through a bed of celite
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ea186d174e804d59ae6240a0c212c3c5
Source dataset
uspto-grants-1986_05
Patent number
US04588821

Reaction notes

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