Imidazole → HCID 131730158, compound

HRID 1806971Notes

Reaction equation

HRID 1806971 reaction equation
[CH2:1]([C:3](CO)([CH2:7][CH3:8])[CH2:4][C:5]#N)[CH3:2].N1[CH:15]=[CH:14][N:13]=C1.[C:16]([Si:20](C)(C)Cl)([CH3:19])([CH3:18])[CH3:17].[OH2:24].Cl[CH2:26]Cl>>[C:16]([SiH2:20][O:24][C:1]([CH3:2])([CH3:26])[C:3]([CH2:4][CH3:5])([CH2:7][CH3:8])[CH2:15][C:14]#[N:13])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 962WaterHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 866404003-Ethyl-3-(hydroxymethyl)pentanenitrile

Product 1

HCID 131730158HCID 131730158, compoundYield 74%

Procedure

Step C To the solution of 3-ethyl-3-hydroxymethyl-pentanenitrile (1.7 g, 12 mmol) and imidazole (1.2 g, 18 mmol) in dichloromethane (80 mL) was added tert-butyldimethylchlorosilane (2 g, 13 mmol). The reaction mixture was stirred at room temperature for 2 h. Water was added. The organic layer was separated, the aqueous layer was then extracted with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, concentrated to give 3-(tert-butyl-dimethyl-silanyloxymethyl)-3-ethyl-pentanenitrile as a colorless oil (2.28 g, 74%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was then extracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-687b4f5937e140e285f18dfbeb95fcc9
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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