Imidazole → HCID 22557710, compound

HRID 984415Notes

Reaction equation

HRID 984415 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[Br:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[CH2:18][OH:19])=[CH:12][CH:11]=1.N1C=CN=C1>ClCCl.Cl>[Br:9][C:10]1[CH:11]=[CH:12][C:13](/[CH:16]=[CH:17]/[CH2:18][O:19][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11183465(2E)-3-(4-bromophenyl)prop-2-en-1-ol

Product 1

HCID 22557710HCID 22557710, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl chlorodimethylsilane (1.33 g, 19.5 mmol) was added to a stirred solution of (E)-3-(4-bromo-phenyl)-prop-2-en-1-ol (3.20 g, 15.0 mmol), and imidazole (2.72 g, 18.0 mmol) in dry dichloromethane (75 ml) and the resulting mixture stirred at room temperature for 18 h, a colourless precipitate being formed. The mixture was diluted with dichloromethane (100 ml) and 1N hydrochloric acid (100 ml). The aqueous layer was separated, further extracted with dichloromethane (2×100ml) and the combined organic layers washed with brine, dried (MgSO4) and evaporated. The product was purified by column chromatography on silica gel (1% diethyl ether in n-heptane eluent) to give the colourless solid, (E)-[3-(4-bromo-phenyl)-allyloxy]-tert-butyldimethylsilane (4.39 g, 89%).

Workup

  1. customa colourless precipitate being formed
  2. customThe aqueous layer was separated
  3. extractionfurther extracted with dichloromethane (2×100ml)
  4. washthe combined organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe product was purified by column chromatography on silica gel (1% diethyl ether in n-heptane eluent)

Sources & evidence

ORD record
ord-4cea974f9ce445a3957eaddfe0f4c1ba
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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