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

HRID 1421778Notes

Reaction equation

HRID 1421778 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-8212459b874147968db44ed80c3fa3a4
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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