Imidazole → 4-{[tert-Butyl(diphenyl)silyl]oxy}cyclohexane-1-carbonitrile

HRID 2260412Notes

Reaction equation

HRID 2260412 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH2:4][CH2:3]1.[CH3:10][C:11]([Si:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])[CH3:12].N1C=CN=C1.[Na+].[Cl-]>CN(C)C=O.O>[CH3:13][C:11]([Si:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[O:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]#[N:9])[CH2:4][CH2:3]1)([CH3:10])[CH3:12]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 5234Sodium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 126172724-Hydroxycyclohexanecarbonitrile

Product 1

HCID 189995484-{[tert-Butyl(diphenyl)silyl]oxy}cyclohexane-1-carbonitrileYield 85.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution maintained at 10° C., under nitrogen, of 11 g (87.8 mmoles) of 4-hydroxycyclohexanecarbonitrile (prepared according to Praefcke K. and Schmidt D., Z. Naturforsch (1980) 35b, 1451-4) in 50 ml of N,N-dimethylformamide, there is added dropwise 26.6 g (96.8 mmoles) of 1,1-dimethylethyldiphenylsilyl chloride, then by portions, 13.1 g (190 mmoles) of imidazole. Stirring is continued at room temperature during 3 days, before pouring the reaction mixture in water saturated with NaCl. The product is extracted with a hexane-ether (1:1) mixture. The organic phase is washed with a N HCl solution, then with water saturated with NaCl, before drying and concentration. The residue is purified by chromatography on a column of silica in dichloromethane to give 26.5 g (yield=85.9%) of a colorless thick oil.

Workup

  1. extractionThe product is extracted with a hexane-ether (1:1) mixture
  2. washThe organic phase is washed with a N HCl solution
  3. dry with materialwith water saturated with NaCl, before drying
  4. concentrationconcentration
  5. customThe residue is purified by chromatography on a column of silica in dichloromethane

Sources & evidence

ORD record
ord-24a3e16e6ad14cf2a3e89a845ba64811
Source dataset
uspto-grants-1995_12
Patent number
US05476846

Reaction notes

Loading…