Iodoethane → 8-Ethoxy-1,4-dioxaspiro[4.5]decane

HRID 511393

Reaktionsgleichung

Reaktionsgleichung von HRID 511393
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH2:14](I)[CH3:15]>C1COCC1>[CH2:14]([O:13][CH:10]1[CH2:11][CH2:12][C:7]2([O:6][CH2:5][CH2:4][O:3]2)[CH2:8][CH2:9]1)[CH3:15]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Produkt 1

HCID 5673588-Ethoxy-1,4-dioxaspiro[4.5]decaneAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (506 mg, 12.65 mmol) was added to a solution of 1,4-Dioxa-spiro[4.5]decan-8-ol (2 gm, 12.65 mmol) in dry THF (20 mL) at 0° C. After 15 minutes, ethyl iodide (2 gm, 12.65 mmol) was added and the mixture was allowed to stir at RT overnight. After removing the THF under reduced pressure, the mixture was poured into ice cold water and extracted into ethyl acetate. The crude product was purified by flash column chromatography (EtOAc:Hexane 5:95) to isolate the title compound (1.3 gm, 55%). 1H NMR (CDCl3, 500 MHz): δ 1.2 (t, 3H, J=7), 1.45-1.92 (m, 8H), 3.4 (m, 1H), 3.45 (m, 2H), 3.98 (m, 4H).

Aufarbeitung

  1. customAfter removing the THF under reduced pressure
  2. additionthe mixture was poured into ice cold water
  3. extractionextracted into ethyl acetate
  4. customThe crude product was purified by flash column chromatography (EtOAc:Hexane 5:95)

Quellen und Nachweise

ORD-Eintrag
ord-2df7781d5a694dc9a9419684deeef762
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096624B2

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