Acetonitrile → Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate

HRID 1253319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253319
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[O:13]1[C:17]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].C(#N)C>O.CCOCC>[CH2:9]([O:8][C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([N:20]2[CH2:21][CH2:22][C:17]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:18][CH2:19]2)=[CH:3][CH:4]=1)[CH3:10]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Produkt 1

HCID 12717439Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoateAusbeute 30,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 50 g (0.349 mol) of ethyl p-fluorobenzoate, 185 g (1.29 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, 73 g (0.5282 mol) of K2CO3, and 400 ml of acetonitrile is stirred at 90°-100° C. for three days. The reaction mixture is allowed to cool to ambient temperature, diluted with water, and extracted with methylene chloride. The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo to give a pasty solid. Trituration with ether furnishes 31 g (23%) of title compound: IR (KBr) 1695 and 1610 cm-1 ; NMR (CDCl3) δ 7.98 (d, 2H), 6.96 (m, 2H), 4.36 (q, 2H), 4.02 (s, 4H), 3.58-3.48 (m, 4H), 1.92-1.80 (m, 4H), and 1.38 (t, 3H).

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a pasty solid

Quellen und Nachweise

ORD-Eintrag
ord-3cb8a5b196e74a84a7f846a41fb4e4e0
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04748246

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