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

HRID 129083Notes

Reaction equation

HRID 129083 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-049f11e465fb45b2b295bea85faaf69b
Source dataset
uspto-grants-1995_11
Patent number
US05466687

Reaction notes

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