Sodium hydride → 1-Tert-butyl 5-ethyl 2-[(acetyloxy)acetyl]pentanedioate

HRID 2250635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250635
[H-].[Na+].[C:3]([O:6][CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:5])[CH3:4].I[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1>[C:3]([O:6][CH2:7][C:8]([CH:9]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:17])(=[O:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 10911297Ethyl 3-iodopropanoateHCID 57260374Tert-butyl 4-(acetyloxy)-3-oxobutanoate

Produkt 1

HCID 574813831-Tert-butyl 5-ethyl 2-[(acetyloxy)acetyl]pentanedioateAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 60% NaH (1.02 g) in THF (50 mL) was added tert-butyl 4-(acetyloxy)-3-oxobutanoate (5.00 g) under ice-water cooling and the mixture was stirred at 0° C. for 0.5 hour. To this added ethyl 3-iodopropanoate (5.54 g) and the mixture was stirred at 50° C. for 8 hours. The mixture was partitioned between AcOEt and water. The organic layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and AcOEt (20:1-3:1) to give 1-tert-butyl 5-ethyl 2-[(acetyloxy)acetyl]pentanedioate as yellow oil (4.27 g).

Aufarbeitung

  1. customThe mixture was partitioned between AcOEt and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of hexane and AcOEt (20:1-3:1)

Quellen und Nachweise

ORD-Eintrag
ord-d6b9ba51eb2544649fd3b323771b8747
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07317009B2

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