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Water → HCID 19429707, Verbindung

HRID 1078492
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1078492
[H-].[Na+].[C:3]12([C:13]3[CH:14]=[C:15]([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[CH:26]=[C:25]([C:30]([O:32][CH3:33])=[O:31])[CH:24]=[CH:23]5)[CH:16]=[CH:17][C:18]=3[OH:19])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[C:34]1([C:40]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[NH:41][CH2:42][CH2:43][CH2:44]Br)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>CN(C=O)C>[C:3]12([C:13]3[CH:14]=[C:15]([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[CH:26]=[C:25]([C:30]([O:32][CH3:33])=[O:31])[CH:24]=[CH:23]5)[CH:16]=[CH:17][C:18]=3[O:19][CH2:44][CH2:43][CH2:42][NH:41][C:40]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:10][CH:9]3[CH2:11][CH:5]([CH2:6][CH:7]([CH2:8]3)[CH2:12]1)[CH2:4]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2565813-Bromo-N-trityl-1-propanamineHCID 10136413HCID 10136413, Verbindung

Produkt 1

HCID 19429707HCID 19429707, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
3×

Versuchsvorschrift

360 mg (12 mmol) of sodium hydride (80% in oil) and 50 ml of DMF are introduced into a three-necked round-bottomed flask. A solution of 4.1 g (10 mmol) of methyl 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthoate in 75 ml of DMF are added dropwise, under a nitrogen stream, and the mixture is stirred until the evolution of gas ceases. A solution of 42 g (11 mmol) of N-triphenylmethyl-3-bromopropylamine in 50 ml of DMF is then introduced dropwise and the mixture is stirred at room temperature for 8 h. The reaction medium is poured into water, extracted with ethyl ether, the organic phase separated after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is purified by silica chromatography, eluted with a dichloromethane and hexane mixture (40-60). After evaporation of the solvents, 4.7 g (66%) of the expected product are recovered, which product melts at 168°-9° C.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 8 h
  2. extractionextracted with ethyl ether
  3. customthe organic phase separated after settling
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by silica chromatography
  9. washeluted with a dichloromethane and hexane mixture (40-60)
  10. customAfter evaporation of the solvents, 4.7 g (66%) of the expected product
  11. customare recovered

Quellen und Nachweise

ORD-Eintrag
ord-2039bef32df54470b5895dc2c9dbcefd
Quelldatensatz
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05547983

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