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Sodium hydride → HCID 15614945, Verbindung

HRID 620357
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 620357
[H-].[Na+].[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:17])([F:16])[F:15])[C:5]=1[C:20]([NH:22][C:23](=[O:26])[O:24][CH3:25])=[O:21].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C1COCC1>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:16])([F:17])[F:15])[C:5]=1[C:20]([N:22]([C:23]([O:24][CH3:25])=[O:26])[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 15614951HCID 15614951, Verbindung

Produkt 1

HCID 15614945HCID 15614945, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Sodium hydride (2.61 g, 6.43 mmol) was added to a stirred solution of N-[[2-bromo-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]carbamic acid, methyl ester (2.61 g, 6.43 mmol) in dry THF (95 mL) at room temperature under a dry N2 atmosphere. After 1 hour, tert-butyl bromoacetate (1.56 mL, 1.5 eq) was added and the reaction mixture was heated at 60° C. for 2.5 hours. The reaction mixture was cooled to room temperature and the THF was removed. Water (100 mL) was added and the resulting solid was filtered. The resulting solid was washed with water and then petroleum ether and dried in vacuo to provide the title compound as a white solid (2.81 g, 84%). A small portion was recrystallized from petroleum ether:ether, m.p. 126°-128° C.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe THF was removed
  3. additionWater (100 mL) was added
  4. filtrationthe resulting solid was filtered
  5. washThe resulting solid was washed with water
  6. dry with materialpetroleum ether and dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2eb977371e2947cda6a3caab0a1f7fcb
Quelldatensatz
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04820727

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