Imidazole → HCID 86617436, compound

HRID 2076703Notes

Reaction equation

HRID 2076703 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[C:17]=2[CH3:29])=[CH:12][CH:11]=1.N1C=CN=C1>CN(C)C=O.C(OCC)(=O)C>[Si:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[C:17]=2[CH3:29])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86241496HCID 86241496, compound

Product 1

HCID 86617436HCID 86617436, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl(dimethyl)silyl chloride (370 mg, 2.48 mmol) was added to a solution of allyl (4′-hydroxy-2-methyl-1,1′-biphenyl-3-yl)acetate (830 mg, 2.48 mmol) obtained in Example (98-1) and imidazole (170 mg, 2.48 mmol) in N,N-dimethylformamide (12 ml), and the mixture was stirred at room temperature for 1 hour. After the reaction mixture was diluted with ethyl acetate and successively washed with water and a saturated aqueous NaCl solution, it was dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=95/5-90/10) to give allyl (4′-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,1′-biphenyl-3-yl)acetate (675 mg, yield: 69%).

Workup

  1. washsuccessively washed with water
  2. dry with materiala saturated aqueous NaCl solution, it was dried with anhydrous sodium sulfate
  3. customThe residue obtained
  4. customby removing the solvent under reduced pressure
  5. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=95/5-90/10)

Sources & evidence

ORD record
ord-3ec8274acf9b471e86ad41b4e07206ac
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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