Imidazole → HCID 10535529, compound

HRID 1427657Notes

Reaction equation

HRID 1427657 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][CH2:15][CH2:16][C:17]#[N:18]>CN(C=O)C>[Si:6]([O:14][CH2:15][CH2:16][C:17]#[N:18])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8011HydracrylonitrileHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10535529HCID 10535529, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (33.6 g, 495 mmol) and tert-butyldimethylsilyl chloride (27.2 g, 180 mmol) were added to a 0° C. solution of 3-hydroxypropanenitrile (10.6 g, 150 mmol) in DMF 50 mL). The mixture was allowed to warm to rt, then was stirred at rt for 12 hrs. The mixture was quenched with water (500 mL), and then extracted with EtOAc (3×). The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (gradient elution 0-5% EtOAc/petroleum ether) to give 3-(tert-butyldimethylsilyloxy) propanenitrile (18 g, 75%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.74 (t, J=6.0 Hz, 2H), 2.43 (t, J=6.0 Hz, 2H), 0.81 (s, 9H), 0.00 (s, 6H).

Workup

  1. customThe mixture was quenched with water (500 mL)
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (gradient elution 0-5% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-851513abfe48454a87635460c7e542a5
Source dataset
uspto-grants-2015_01
Patent number
US08933233B2

Reaction notes

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