Diethyl methylmalonate → HCID 66692023, compound

HRID 330814Notes

Reaction equation

HRID 330814 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:13])[CH:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3].[I:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1>CCO>[CH2:2]([O:4][C:5](=[O:13])[C:6]([CH2:19][C:18]1[CH:21]=[CH:22][C:15]([I:14])=[CH:16][CH:17]=1)([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3]

Participants

5

Reactant 3

HCID 11857Diethyl methylmalonateHCID 9542584-Iodobenzyl bromideHCID 5360545Sodium

Product 1

HCID 66692023HCID 66692023, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

220 mg (10 mmol) sodium in small pieces are added to 15 mL EtOH. After 15 min 1.65 mL (9.70 mmol) 2-methyl-malonic acid diethyl ester are added. The mixture is stirred at reflux for 15 min and subsequently 3.00 g (10.1 mmol) 4-iodobenzyl bromide are added. The mixture is stirred at reflux for 12 h. After that time, the solvent is evaporated and the residue is purified by column chromatography (silicia gel; cyclohexane:EtOAc 98:2) to yield the desired product.

Workup

  1. temperatureat reflux for 15 min
  2. stirringThe mixture is stirred
  3. temperatureat reflux for 12 h
  4. customAfter that time, the solvent is evaporated
  5. customthe residue is purified by column chromatography (silicia gel; cyclohexane:EtOAc 98:2)

Sources & evidence

ORD record
ord-fad36bf0548844f082edb1deef558272
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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