Imidazole → HCID 23001318, compound

HRID 398011Notes

Reaction equation

HRID 398011 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Si:9](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CN=C1>CN(C=O)C>[Si:9]([O:8][C:4]1[CH:3]=[C:2]([I:1])[CH:7]=[CH:6][CH:5]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 122723-IodophenolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 23001318HCID 23001318, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-iodophenol (3.36 g, 15.3 mmol), tert-butyldiphenylsilylchloride (4.17 mL, 16.0 mmol), and imidazole (1.48 g, 21.7 mmol) in DMF (30 mL) was heated to 60° C. for 72 hours. The solvent was removed in vacuo and the residue partitioned between saturated sodium bicarbonate (50 mL) and methylene chloride (50 mL). The layers were separated and the aqueous layer washed with methylene chloride (2×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a yellow oil. The crude product was purified by column chromatography (0→20% ethyl acetate/hexane) to provide the title compound as a clear oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between saturated sodium bicarbonate (50 mL) and methylene chloride (50 mL)
  3. customThe layers were separated
  4. washthe aqueous layer washed with methylene chloride (2×50 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a yellow oil
  9. customThe crude product was purified by column chromatography (0→20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d9edc5c5cc9f494ea75ae6b527b147c0
Source dataset
uspto-grants-2003_08
Patent number
US06610722B2

Reaction notes

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