Imidazole → (1r)-2-Imidazolyl-1-phenylethan-1-ol

HRID 496421Notes

Reaction equation

HRID 496421 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.N1C=CC=CC=1.[CH2:12]1[O:20][C@@H:13]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:12][C@H:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[OH:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 1049PyridineHCID 114705(+)-Styrene oxide

Product 1

HCID 69735309(1r)-2-Imidazolyl-1-phenylethan-1-olYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a manner similar to that of Example 49, step 1, imidazole (2.83 g, 41.6 mmol) is dissolved in absolute ethanol (45 mL). Pyridine (0.11 mL) is added followed by addition of (R)-(+) styrene oxide (5.0 g, 41.6 mol, Aldrich Chemical Co.), followed by heating at reflux for 18 hours. The mixture is evaporated in vacuo to a syrup and suspended between ethyl ether (250 mL) and water (100 mL) to give a solid precipitate. The suspension is filtered and washed with ethyl ether. The solid is recrystallized from hot ethyl acetate and dried in vacuo (2.52 g, 32% yield). MS: APCI: M+1, 189.1 (M: 188.2). NMR spectrum is consistent with structure.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 18 hours
  3. customThe mixture is evaporated in vacuo to a syrup
  4. customto give a solid precipitate
  5. filtrationThe suspension is filtered
  6. washwashed with ethyl ether
  7. customThe solid is recrystallized from hot ethyl acetate
  8. customdried in vacuo (2.52 g, 32% yield)

Sources & evidence

ORD record
ord-150e80cf7b2f4adaa9053a82b1eba305
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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