1-Tritylpiperidin-4-one → 4-[4-(2-Oxazolin-2-yl)benzylidene]-1-tritylpiperidine

HRID 129083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129083
C([Li])CCC.[C:6]([N:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:32]1[CH2:36][CH2:35][N:34]=[C:33]1[C:37]1[CH:51]=[CH:50][C:40]([CH2:41]P(=O)(OCC)OCC)=[CH:39][CH:38]=1>CCCCCC.O1CCCC1>[O:32]1[CH2:36][CH2:35][N:34]=[C:33]1[C:37]1[CH:38]=[CH:39][C:40]([CH:41]=[C:28]2[CH2:27][CH2:26][N:25]([C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:30][CH2:29]2)=[CH:50][CH:51]=1

Komponenten

6

Edukt 3

HCID 27484141-Tritylpiperidin-4-oneHCID 15231401Diethyl 4-(2-oxazolin-2-yl)benzylphosphonateHCID 178418339Butyllithium

Produkt 1

HCID 152314024-[4-(2-Oxazolin-2-yl)benzylidene]-1-tritylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

6.25 ml of a 1.6M solution of n-butyllithium in hexane followed, after stirring for 20 minutes, by 3.4 g of N-trityl-4-piperidone (prepared from 4-piperidone hydrochloride hydrate and trityl chloride) in 20 ml of tetrahydrofuran are added dropwise at -60° C. to 2.97 g of diethyl 4-(2-oxazolin-2-yl)benzylphosphonate. The mixture is stirred at -60° C. for 25 minutes. The reaction solution is then allowed to warm to ambient temperature and is stirred for a further 1.5 hours at this temperature. The reaction solution is then stirred into 150 ml of ice-water, the mixture is extracted three times with 150 ml of ethyl acetate, and the organic phase is dried and evaporated down. The residue is purified by column chromatography on Silica gel (petroleum ether/ethyl acetate=1:1, v/v). 1.7 g of the title compound of melting point 110°-115° C. are obtained.

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. stirringis stirred for a further 1.5 hours at this temperature
  3. extractionthe mixture is extracted three times with 150 ml of ethyl acetate
  4. customthe organic phase is dried
  5. customevaporated down
  6. customThe residue is purified by column chromatography on Silica gel (petroleum ether/ethyl acetate=1:1

Quellen und Nachweise

ORD-Eintrag
ord-049f11e465fb45b2b295bea85faaf69b
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466687

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