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

HRID 860491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860491
[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-cb3ed2a8d94a473e92376235badcd6ad
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153854B2

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