1,4-Dioxaspiro[4.5]decan-8-one → 8-Pyrimidin-2-yl-1,4-dioxa-spiro[4.5]decan-8-ol

HRID 1173265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173265
[SnH3][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[O:13]1[C:17]2([CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1>C1COCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[C:20]1([OH:23])[CH2:21][CH2:22][C:17]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:18][CH2:19]1

Komponenten

5

Edukt 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 871506562-Stannyl pyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 590174338-Pyrimidin-2-yl-1,4-dioxa-spiro[4.5]decan-8-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2-stannyl pyrimidine (200 mmol, 80 g), prepared as previously described in the literature (Tetrahedron, 1994, 50, 275-284), in THF (1 L) was added n-butyllithium (240 mmol, 150 mL) at −78° C. The reaction was stirred for 30 min at −78° C. and 1,4-dioxa-spiro[4.5]decan-8-one (200 mmol, 30 g) was added. The reaction was allowed to stir overnight while warming to ambient temperature. The reaction was then quenched using NH4Cl and extracted using EtOAc (3×400 mL). The organic layers were combined and dried over MgSO4 and concentrated in vacuo. The crude was taken to the next step.

Aufarbeitung

  1. stirringto stir overnight
  2. temperaturewhile warming to ambient temperature
  3. customThe reaction was then quenched
  4. extractionextracted
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6ceb8cd83c74973a52197b11088a518
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834021B2

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