Sodium Hydroxide → (E)-2-acetamido-2-(2-butenyl)malonic acid

HRID 362151Notes

Reaction equation

HRID 362151 reaction equation
[C:1]([NH:4][C:5]([CH2:16]/[CH:17]=[CH:18]/[CH3:19])([C:11]([O:13]CC)=[O:12])[C:6]([O:8]CC)=[O:7])(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C.O>[C:1]([NH:4][C:5]([CH2:16]/[CH:17]=[CH:18]/[CH3:19])([C:11]([OH:13])=[O:12])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86753714diethyl (E)-2-acetamido-2-(2-butenyl)malonate

Product 1

HCID 19364638(E)-2-acetamido-2-(2-butenyl)malonic acidYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

39.63 g (146 mmol) of diethyl (E)-2-acetamido-2-(2-butenyl)malonate were dissolved in 200 ml of ethanol and a solution of 19.24 g (481 mmol) of sodium hydroxide in 100 ml of water was added. The mixture was stirred for 2 hours at 60° C., evaporated to dryness under a vacuum and theresidue was partitioned between diethyl ether and water. The aqueous phase was acidified with 2M hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and the solvent was removed by evaporation under a vacuum to give 26.1 g of (E)-2-acetamido-2-(2-butenyl)malonic acid as a white solid which was used in the next step without further purification. 1 H NMR (250 MHz, MeOD) δ: 1.65 (d, 3 H), 2.0 (s, 3 H), 2.9 (d, 2 H), 5.25 (m, 1 H), 5.5 (m,1 H).

Workup

  1. customevaporated to dryness under a vacuum
  2. customwas partitioned between diethyl ether and water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. customthe solvent was removed by evaporation under a vacuum

Sources & evidence

ORD record
ord-4df2a8d1ed1646ddb22a703c1b51a935
Source dataset
uspto-grants-1999_02
Patent number
US05866684

Reaction notes

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