Imidazole → HCID 131735123, compound

HRID 929762Notes

Reaction equation

HRID 929762 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6](CO)=[CH:5][CH:4]=1)#[N:2].N1C=CN=[CH:12]1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])(C)C.OS([O-])(=O)=O.[K+].CCO[C:33]([CH3:35])=[O:34]>CN(C=O)C.CCCCCC>[C:19]([SiH2:16][O:34][C:33]([CH3:35])([CH3:12])[C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 160549p-Cyanobenzyl alcoholHCID 516920Potassium bisulfate

Product 1

HCID 131735123HCID 131735123, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4-cyanobenzyl alcohol (5.0 g, 37.9 mmol) in DMF was added imidazole (2.79 g, 41 mmmol) and tert-butyldimethylsilyl chloride (6.2 g, 41 mmol). After stirring for 14 h, the reaction mixture was poured into 0.1M aqueous KHSO4 and extracted three times with diethyl ether. The combined organic phases were washed twice with water, once with brine and dried over MgSO4. Filtration followed by removal of volatiles under reduced pressure gave crude product. Flash chromatography (10% EtOAc in hexane) provided 4-(tert-butyl-dimethyl-silanyloxymethyl)-benzonitrile as a white solid (3.41 g, 36%). 1H NMR (300 MHz, CDCl3) δ ppm 7.57 (d, 2H), 7.36 (d, 2H), 4.68 (d, 2H), 0.82 (s, 9H), 0.02 (2, 6H).

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe combined organic phases were washed twice with water, once with brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration
  5. customfollowed by removal of volatiles under reduced pressure
  6. customgave crude product

Sources & evidence

ORD record
ord-7849abe1ded04ad989b5d5ae35ca732f
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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