Benzophenone → HCID 13825793, compound

HRID 2352427Notes

Reaction equation

HRID 2352427 reaction equation
C([Li])CCC.CCCCCC.[CH2:12]([O:19][C:20]1[CH:31]=[CH:30][C:23]([CH2:24][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(CCN(C)C)C.[C:40]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1.O>[CH2:12]([O:19][C:20]1[CH:31]=[CH:30][C:23]([CH:24]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[C:40]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[OH:47])=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 3102BenzophenoneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 183532481-{[4-(Benzyloxy)phenyl]methyl}-1H-imidazoleHCID 178418244HCID 178418244, compound

Product 1

HCID 13825793HCID 13825793, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

34 ml (53 mmol) of 1,55 molar n-butyllithium/hexane solution were added dropwise to a solution of 6.87 g (26 mmol) of N-(4-benzyloxybenzyl)-imidazole and 3.03 g (26 mmol) of TMEDA in 100 ml of absolute THF at about -70° C., the mixture was stirred for 20 minutes at -70° C., a solution of 4.74 g of benzophenone in 40 ml of absolute THF was then added dropwise at -70° C., stirring was continued for 30 minutes at about -70° C. and for 1.5 hours at -70° C. to room temperature, and 350 ml of water were added, while cooling. The mixture was extracted with CH2Cl2. The residue (12 g) from the CH2Cl2 extract was chromatographed over a silica gel S/CH2Cl2 column (diameter 2.1 cm, height 55 cm) as described in Example 102. Fractions which were shown by thin layer chromatography to have a high concentration of the desired substance were combined and recrystallized from ethyl acetate/diisopropyl ether. 1.09 g (=16.4% yield) of pure 2-(4-benzyloxyphenyl)-2-(1-imidazolyl)-1,1-diphenylethanol of melting point 204° C. were obtained in this manner.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes at about -70° C. and for 1.5 hours at -70° C. to room temperature
  3. temperaturewhile cooling
  4. extractionThe mixture was extracted with CH2Cl2
  5. extractionThe residue (12 g) from the CH2Cl2 extract
  6. customwas chromatographed over a silica gel S/CH2Cl2 column (diameter 2.1 cm, height 55 cm)
  7. concentrationa high concentration of the desired substance
  8. customrecrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-5694af3fb33f4528befe57da117ec330
Source dataset
uspto-grants-1989_10
Patent number
US04876354

Reaction notes

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