Acetonitrile → 8-(4-(Methylsulfonyl)phenyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 329927

Reaktionsgleichung

Reaktionsgleichung von HRID 329927
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].[O:18]1[C:22]2([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[O:21][CH2:20][CH2:19]1.C(#N)C>O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:25]2[CH2:26][CH2:27][C:22]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:23][CH2:24]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 679941-Fluoro-4-(methylsulphonyl)benzene

Produkt 1

HCID 42563608-(4-(Methylsulfonyl)phenyl)-1,4-dioxa-8-azaspiro[4.5]decaneAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 10 g (0.057 mol) of p-fluorophenyl methyl sulfone, 8.72 g (0.063 mol) of K2CO3, 24.66 g (0.172 mol) of 1,4-dioxa-8-azaspiro[4.5]-decane and 50 ml of acetonitrile is stirred overnight at 90°-100° C. After cooling, the mixture is diluted with water and extracted with methylene chloride. The combined extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo. Trituration with ethyl ether affords 13.11 g (77%) of title compound as a white solid: m.p. 192°-194° C.; IR (KBr) 1588, 1369, and 1290 cm-1 ; NMR (CDCl3) δ 7.74 (m, 2H), 6.96 (m, 2H), 4.02 (s, 4H), 3.54 (m, 4H), 3.03 (s, 3H), and 1.81 (m, 4H).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7a0af4ea29a74a42902eadeffd979f2f
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04894374

Verknüpfte Notizen

Wird geladen…