Potassium Carbonate → 1-Tert-butyl 7-ethyl 2-(methoxyacetyl)heptanedioate

HRID 860428Notes

Reaction equation

HRID 860428 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:13])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O>[CH3:1][O:2][CH2:3][C:4]([CH:5]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:6]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4169827Ethyl 5-iodopentanoateHCID 206361091,1-Dimethylethyl 4-methoxy-3-oxobutanoate

Product 1

HCID 574813401-Tert-butyl 7-ethyl 2-(methoxyacetyl)heptanedioateYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of tert-butyl 4-methoxy-3-oxobutanoate (3.09 g) and potassium carbonate (2.50 g) in dimethylformamide (20 mL) was added ethyl 5-iodopentanoate (4.62 g) and the mixture was stirred at ambient temperature for 15 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (20:1-5:1) to give 1-tert-butyl 7-ethyl 2-(methoxyacetyl)heptanedioate as colorless oil (4.33 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of hexane and ethyl acetate (20:1-5:1)

Sources & evidence

ORD record
ord-11821cc61e0c4570b35d91bcdbff0a84
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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