Imidazole → 4'-{[Tert-butyl(dimethyl)silyl]oxy}-2',6'-dimethylbiphenyl-3-carbaldehyde

HRID 2280634Notes

Reaction equation

HRID 2280634 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1>CN(C)C=O>[Si:18]([O:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 231116914'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehyde

Product 1

HCID 598383304'-{[Tert-butyl(dimethyl)silyl]oxy}-2',6'-dimethylbiphenyl-3-carbaldehydeYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4′-Hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde 3d (7.20 g, 31.80 mmol, prepared by a method disclosed in Chinese patent application CN101616913), tert-butyldimethylsilyl chloride (5.27 g, 34.90 mmol), and imidazole (2.60 g, 38.10 mmol) were dissolved in 60 mL of N,N-dimethylformamide. The reaction solution was heated to 60° C. and stirred for 12 hours. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound 4′-((tert-butyldimethylsilyl)oxy)-2′,6′-dimethylbiphenyl-3-carbaldehyde 3e (10 g, yield 92.0%) as a brown oil.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-82f5f1e810fd4d7fa701a781fed8a12f
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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