Ethyl 2-methylacetoacetate → Diethyl 2-acetyl-2-methyloctanedioate

HRID 1486360Notes

Reaction equation

HRID 1486360 reaction equation
[CH3:1][CH:2]([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-][CH2:12]C.[Na+].BrC[CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:1][C:2]([CH3:12])([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4])([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 117544Ethyl 6-bromohexanoateHCID 2723922Sodium ethoxide

Product 1

HCID 22266834Diethyl 2-acetyl-2-methyloctanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 25 g of ethyl 2-methylacetoacetate, 64 mL of a 21% sodium ethoxide solution in ethanol and 34 mL of ethyl 6-bromohexanoate is refluxed in 200 mL of ethanol overnight. The mixture is filtered and solvent is evaporated. The residue is partitioned between 1 M HCl and chloroform. The organic layer is dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/hexanes as eluant to yield 22 g of ethyl 2-(5-carbethoxypentyl)-2-methylacetoacetate.

Workup

  1. filtrationThe mixture is filtered
  2. customsolvent is evaporated
  3. customThe residue is partitioned between 1 M HCl and chloroform
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. custompurified on silica gel using 1:10 ethyl acetate/hexanes as eluant

Sources & evidence

ORD record
ord-56f1edc22a8b479a86c92daeed6ff5ee
Source dataset
uspto-grants-2016_08
Patent number
US09423323B2

Reaction notes

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