Imidazole → HCID 66692833, compound

HRID 1469187Notes

Reaction equation

HRID 1469187 reaction equation
[I:1][C:2]1[S:6][C:5]([CH3:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18].N1C=CN=C1>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:17]([Si:20]([O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:4]2[CH:3]=[C:2]([I:1])[S:6][C:5]=2[CH3:7])=[CH:10][CH:11]=1)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:16]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 66692923HCID 66692923, compound

Product 1

HCID 66692833HCID 66692833, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of phenol 23 (0.54 g, 1.64 mmol) in DMF (15 mL) were added TBDMSCl (1M in CH2Cl2, 3.5 mL, 3.28 mmol), imidazole (0.35 g, 4.92 mmol) and DMAP (50 mg, 0.33 mmol) at room temperature. The mixture was stirred at ambient temperature for 15 hours. The mixture was extracted with EtOAc/H2O (50 mL/150 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the title compound 24 (0.65 g, 89%).

Workup

  1. extractionThe mixture was extracted with EtOAc/H2O (50 mL/150 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-85b4976c7f8348588ab29d25735c6c63
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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