Imidazole → 4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 273033Notes

Reaction equation

HRID 273033 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C>[Si:16]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 685766664-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (5 g, 25 mmol), t-butyldimethylsilyl chloride (4.46 g, 29 mmol) and imidazole (2.34 g, 34 mmol) were stirred in DMF (15 ml) at room temperature. After 30 minutes, a yellow suspension was observed. The reaction was partitioned between ether (75 ml) and water (100 ml). The ether was then washed further with water (4×50 ml), dried over sodium sulphate, filtered and concentrated in vacuo. The title compound was isolated as a pale orange waxy solid (7 g, 90%).

Workup

  1. customThe reaction was partitioned between ether (75 ml) and water (100 ml)
  2. washThe ether was then washed further with water (4×50 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c69f722ccff4755ae329e68e7f9deb8
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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