Реакция #1605855

Уравнение реакции

diisopropyl azodicarboxylate

(2′,6′-dimethyl-[1,1′-biphenyl]-3-yl)methanol

4-hydroxybenzaldehyde

triphenylphosphine

→

title compound

Выход 80.5%

4-((2′,6′-dimethyl-[1,1′-biphenyl]-3-yl)methoxy)benzaldehyde

Выход 80.5%

Растворители

toluene

tetrahydrofuran

toluene

Условия реакции

Обработка

1. 1
   Температураcooling
2. 2
   Другоеthe resultant reaction mixture
3. 3
   Температураcooling for 3 hours
4. 4
   Другоеthe resultant reaction mixture
5. 5
   workup.STIRRINGwas stirred at room temperature for 12 hours
6. 6
   workup.DISTILLATIONFrom the reaction mixture, the solvent was distilled off under reduced pressure
7. 7
   Другоеto give a residue and water
8. 8
   ЭкстракцияThe mixture was extracted with an organic solvent
9. 9
   Сушкаthe resultant organic phase was dried over anhydrous sodium sulfate
10. 10
    workup.DISTILLATIONFrom the organic phase, the solvent was distilled off under reduced pressure
11. 11
    Другоеthe resultant residue was purified by silica gel column chromatography (eluent; n-heptane:ethyl acetate=100:0 to 100:20)

Методика

To a solution of (2′,6′-dimethyl-[1,1′-biphenyl]-3-yl)methanol (1.0 g), 4-hydroxybenzaldehyde (0.58 g), and triphenylphosphine (1.48 g) in tetrahydrofuran (10 mL), a solution of 40% diisopropylazodicarboxylic acid diisopropyl in toluene (1.09 mL) was added under ice-cooling and the resultant reaction mixture was stirred under ice-cooling for 3 hours. A solution of diisopropyl azodicarboxylate in toluene (0.6 mL) was further added and the resultant reaction mixture was stirred at room temperature for 12 hours. From the reaction mixture, the solvent was distilled off under reduced pressure to give a residue and water was added to the resultant residue. The mixture was extracted with an organic solvent and the resultant organic phase was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; n-heptane:ethyl acetate=100:0 to 100:20) to give the title compound (1.2 g) as a colorless oil.

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