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

HRID 860428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860428
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 574813401-Tert-butyl 7-ethyl 2-(methoxyacetyl)heptanedioateAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-11821cc61e0c4570b35d91bcdbff0a84
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153854B2

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