Реакция #975

Уравнение реакции

4-phenyl-1-butanal

4-Phenyl-1-butanal

3-phenyl-1-propylmagnesium bromide

3-Phenyl-1-propylmagnesium bromide

→

alcohol

Выход 88.8%

1,7-Diphenyl-4-heptanol

Выход 88.8%

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was then quenched by the dropwise addition of saturated NH4Cl
2. 2
   workup.ADDITIONdiluted with ether
3. 3
   ДругоеThe phases were separated
4. 4
   Промывкаthe organic layer was washed with water and brine
5. 5
   Сушкаdried over MgSO4
6. 6
   КонцентрированиеConcentration

Методика

To a solution of 700 mg (4.7 mmol) of 4-phenyl-1-butanal (119) in 5.0 mL of THF at 0° C. was added 10.0 mL (5.0 mmol) of 3-phenyl-1-propylmagnesium bromide (120) and the resulting mixture was stirred at 0° C. for 0.5 h. The mixture was then quenched by the dropwise addition of saturated NH4Cl and diluted with ether. The phases were separated and the organic layer was washed with water and brine and then dried over MgSO4. Concentration gave 1.12 g of the alcohol 121 as an oil. 1H NMR spectrum was consistent with the structure.

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