Water → HCID 58238617, Verbindung

HRID 1037661

Reaktionsgleichung

Reaktionsgleichung von HRID 1037661
[Li]CCCC.[C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18]([O:25][C:26]1[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=1[C:28](N(C)C)=[O:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C1COCC1>[CH2:18]([O:25][C:26]1[CH:36]=[CH:35][CH:34]=[CH:33][C:27]=1[C:28]([C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:13]=1)=[O:29])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 138872-PhenylpyridineHCID 130736022-(Benzyloxy)-N,N-dimethylbenzamideHCID 178418339Butyllithium

Produkt 1

HCID 58238617HCID 58238617, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution of 12.9 g (145 mmol) of 2-N,N-dimethylaminoethanol in 100 mL of hexanes, 116 mL (290 mmol) of 2.5 M nBuLi in hexanes was added dropwise with vigorous stirring at −10° C. This mixture was slowly warmed to 0° C., stirred for 30 min, and then 7.54 g (48.6 mmol) of 2-phenylpyridine was added at −10° C. The resulting mixture was stirred for 2 hr at 0° C. and then added dropwise to a solution of 43.2 g (179 mmol) of 16 in 725 mL of THF at −10° C. This mixture was slowly warmed to room temperature, stirred for 12 hr, and then 20 mL of water was added. The organic solvent was evaporated using a rotary evaporator. 17 was isolated from the residue by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-ethyl acetate=5:1, vol.). The obtained product was additionally washed with 30 mL of diethyl ether and then dried in vacuum. Yield 11.0 g (62%) of white solid.

Aufarbeitung

  1. temperatureThis mixture was slowly warmed to 0° C.
  2. stirringstirred for 30 min
  3. stirringThe resulting mixture was stirred for 2 hr at 0° C.
  4. temperatureThis mixture was slowly warmed to room temperature
  5. stirringstirred for 12 hr
  6. customThe organic solvent was evaporated
  7. customa rotary evaporator
  8. custom17 was isolated from the residue by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-ethyl acetate=5:1, vol.)
  9. washThe obtained product was additionally washed with 30 mL of diethyl ether
  10. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9bdd5276b70641d8812383502fc6351c
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546501B2

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