Pyridine → 4-(3-Hydroxy-1-imidazol-1-yl-propyl)-benzonitrile

HRID 1585951Notes

Reaction equation

HRID 1585951 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][CH:9]([C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1)[N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)(C)(C)C.N1C=CC=CC=1>C(#N)C>[OH:6][CH2:7][CH2:8][CH:9]([C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1)[N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 1049PyridineHCID 187797914-[3-(Tert-butyl-dimethyl-silanyloxy)-1-imidazol-1-yl-propyl]-benzonitrile

Product 1

HCID 187796904-(3-Hydroxy-1-imidazol-1-yl-propyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 4-[3-(tert-butyl-dimethyl-silanyloxy)-1-imidazol-1-yl-propyl]-benzonitrile (2.0 gm, mmol) was suspended in acetonitrile (20 mL) in a teflon flask and HF/pyridine (4 mL) was added and the reaction was stirred for 1 hour. The reaction was quenched with cold aqueous sodium hydroxide and the resulting solution was concentrated in vacuo. The residue was dissolved in methylene chloride and chromatographed on silica gel eluting with 1:1 ethyl acetate:hexanes. The desired fractions were concentrated in vacuo to give the desired product as an oil.

Workup

  1. customThe reaction was quenched with cold aqueous sodium hydroxide
  2. concentrationthe resulting solution was concentrated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride
  4. customchromatographed on silica gel eluting with 1:1 ethyl acetate
  5. concentrationThe desired fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-07805fec8aa6470585a7effd5078d09b
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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