Imidazole → HCID 57443556, compound

HRID 547107Notes

Reaction equation

HRID 547107 reaction equation
N1C=CN=C1.[CH3:6][O:7][C:8](=[O:18])[CH2:9][C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([OH:17])[CH:11]=1.ClCCl.[C:22]([Si:26](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])([CH3:24])[CH3:23]>O1CCCC1>[CH3:6][O:7][C:8](=[O:18])[CH2:9][C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([O:17][Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 94078tert-ButyldiphenylchlorosilaneHCID 579787Methyl 3,5-dihydroxyphenylacetate

Product 1

HCID 57443556HCID 57443556, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Imidazole (230 mg, 3.38 mmol) was added to a solution of 3,5-dihydroxyphenylacetic acid methyl ester (530 mg, 2.91 mmol) in tetrahydrofuran (6.7 mL)-dichloromethane (6.7 mL) at room temperature. t-Butylchlorodiphenylsilane (0.75 mL, 2.9 mmol) was added under cooling with ice. Then, the ice bath was removed, and the mixture was stirred at room temperature for three hours. The reaction mixture was diluted with diethyl ether. 50% saturated aqueous ammonium chloride was added, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to give the title compound (470 mg, 33%).

Workup

  1. temperatureunder cooling with ice
  2. customThen, the ice bath was removed
  3. additionThe reaction mixture was diluted with diethyl ether
  4. addition50% saturated aqueous ammonium chloride was added
  5. extractionfollowed by extraction with diethyl ether
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-0d2399889fa54645b076035bd736172d
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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