Imidazole → HCID 57475822, compound

HRID 2060781Notes

Reaction equation

HRID 2060781 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:15])[CH2:9][CH:10]([OH:14])[CH2:11][CH:12]=[CH2:13])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22]>CN(C=O)C.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:15])[CH2:9][CH:10]([O:14][Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27])[CH2:11][CH:12]=[CH2:13])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57475783HCID 57475783, compound

Product 1

HCID 57475822HCID 57475822, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3-bromophenyl)-3-hydroxyhex-5-en-1-one (9.08 g, 33.7 mmol), 1H-imidazole (5.34 g, 77.6 mmol) and tert-butyldimethylchlorosilane (6.29 g, 40.5 mmol) in DMF (40 mL) is stirred at room temperature for 2 h. The mixture is diluted with dichloromethane and is washed sequentially with water and saturated ammonium chloride aqueous solution. The organic layer is dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product is purified by silica gel chromatography eluting with a linear gradient of 0% to 5% ethyl acetate in hexanes over 20 minutes to give the title compound as a racemic mixture (11.3 g, 88%). ES/MS m/e (79Br/81Br) 383, 385 (M+1).

Workup

  1. washis washed sequentially with water and saturated ammonium chloride aqueous solution
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by silica gel chromatography
  6. washeluting with a linear gradient of 0% to 5% ethyl acetate in hexanes over 20 minutes

Sources & evidence

ORD record
ord-ba2c4f368c2a440b9b7af00c854f9d7f
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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