Water → 1-(1-Adamantyl)-2-(3-chlorophenyl)-2-(1-imidazolyl)-ethanol

HRID 1493740Notes

Reaction equation

HRID 1493740 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[CH:19]([C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2)=[O:20].O>CCCCCC.C1COCC1>[C:21]12([CH:19]([OH:20])[CH:10]([C:9]3[CH:16]=[CH:17][CH:18]=[C:7]([Cl:6])[CH:8]=3)[N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)[CH2:28][CH:27]3[CH2:26][CH:25]([CH2:24][CH:23]([CH2:29]3)[CH2:22]1)[CH2:30]2

Participants

7

Reactant 4

HCID 962WaterHCID 110410501-AdamantanecarboxaldehydeHCID 122293861-(3-Chlorobenzyl)imidazoleHCID 178418339Butyllithium

Product 1

HCID 150528881-(1-Adamantyl)-2-(3-chlorophenyl)-2-(1-imidazolyl)-ethanolYield 30.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

15.5 ml (23 mmol) of a 1.5 molar solution of n-butyl-lithium in hexane were added dropwise to a solution of 3.85 g (20 mmol) of N-(3-chlorobenzyl)-imidazole in 46 ml of absolute THF at -70° C. The mixture was stirred for 30 minutes at -70° C., after which a solution of 3.20 g (20 mmol) of 1-formyladamantane in 20 ml of absolute THF was added dropwise at -70° C. Stirring was continued for 1 hour at about -70° C. and for 2 hours at about -70° C. to room temperature, 120 ml of water were added at about 10° C., while cooling, and the suspension formed was stirred for 1.5 hours at 5°-8° C. Thereafter, the crystalline substance (crude product) was filtered off under suction and rinsed with water and hexane, and the crystalline product, dissolved in CH2Cl2, was filtered over a silica gel/CH2Cl2 column (diameter 2.0 cm, height 20 cm). The filtered solution was evaporated down in vacuo and the residue (2.36 g) was crystallized from acetone. 2.15 g (=30.1% yield) of pure 1-(1-adamantyl)-2-(3-chlorophenyl)-2-(1-imidazolyl)-ethanol of melting point 115° C. were obtained.

Workup

  1. stirringStirring
  2. waitwas continued for 1 hour at about -70° C. and for 2 hours at about -70° C. to room temperature
  3. temperaturewhile cooling
  4. customthe suspension formed
  5. stirringwas stirred for 1.5 hours at 5°-8° C
  6. filtrationThereafter, the crystalline substance (crude product) was filtered off under suction
  7. washrinsed with water and hexane
  8. dissolutionthe crystalline product, dissolved in CH2Cl2
  9. filtrationwas filtered over a silica gel/CH2Cl2 column (diameter 2.0 cm, height 20 cm)
  10. customThe filtered solution was evaporated down in vacuo
  11. customthe residue (2.36 g) was crystallized from acetone

Sources & evidence

ORD record
ord-4cc0b6e003aa4c56bb2b96be6d83a2ca
Source dataset
uspto-grants-1991_06
Patent number
US05023357

Reaction notes

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