Diethyl methylmalonate → HCID 18938318, compound

HRID 357673Notes

Reaction equation

HRID 357673 reaction equation
[CH3:1][CH:2]([C:8](OCC)=O)[C:3]([O:5]CC)=[O:4].[Na].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1CBr.[OH-].[K+]>O>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:21]=[CH:24][CH:25]=[CH:26][C:27]=1[CH2:8][CH:2]([CH3:1])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 11857Diethyl methylmalonateHCID 14797Potassium HydroxideHCID 5360545SodiumHCID 18315540HCID 18315540, compound

Product 1

HCID 18938318HCID 18938318, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

148 g (0.85 mol) of diethyl methylmalonate were added dropwise at room temperature to 19.5 g (0.85 mol) of sodium in 400 cm3 of H2 O-free EtOH. Subsequently, 211 g (0.85 mol) of 2-(2-pyridyl)benzyl bromide were added dropwise and the mixture was heated under reflux for 3 hours. At room temperature, 143 g (2.55 mol) of KOH dissolved in 500 cm3 of H2O were added and the mixture was heated under reflux for a further 4 hours. The EtOH was distilled off and the residue was admixed with H2O until completely dissolved and subsequently acidified with concentrated aqueous HCl to a pH of 1. The precipitate formed was filtered off with suction, dried and heated for 1 hour at 130° C. This gave 193 g (94%) of 2-(2-(2-pryridyl)benzyl)propionic acid as solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. additionwere added
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for a further 4 hours
  6. distillationThe EtOH was distilled off
  7. dissolutionuntil completely dissolved
  8. customThe precipitate formed
  9. filtrationwas filtered off with suction
  10. customdried

Sources & evidence

ORD record
ord-827dc9f3bc9b49a6b42169a5ba4a8ccb
Source dataset
uspto-grants-1998_11
Patent number
US05840947

Reaction notes

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