Hydrochloric Acid → Diethyl methoxymalonate

HRID 628972Notes

Reaction equation

HRID 628972 reaction equation
[C:1]([O:8][CH2:9]C)(=O)[C:2]([O:4][CH2:5][CH3:6])=[O:3].COC[C:14]([O:16][CH3:17])=[O:15].[CH3:18][O-].[Na+].Cl>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:14](=[O:15])[CH:1]([O:8][CH3:9])[C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 80507Methyl methoxyacetateHCID 10942334Sodium Methoxide

Product 1

HCID 575727Diethyl methoxymalonateYield 40.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of diethyl oxalate (27.5 ml, 1 eq.) and methyl methoxyacetate (20 ml, 1 eq.) was added dropwise to a slurry of sodium methoxide (16.4 g, 1.5 eq.) in toluene (350 ml) at 45-50° C. After dropping, the resulting solution was heated to 70-80° C. for 2 hrs and poured into 70 ml of 14% HCl with cooling. The resultant mixture was extracted with EA and the combined organic layers were washed with brine and dried in vacuo to give 16.7 g (40.5%) of a product.

Workup

  1. temperaturewith cooling
  2. extractionThe resultant mixture was extracted with EA
  3. washthe combined organic layers were washed with brine
  4. customdried in vacuo

Sources & evidence

ORD record
ord-244071f195d240bf8d48814402dfcf89
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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