Reaction #975

Reaction equation

4-phenyl-1-butanal

4-Phenyl-1-butanal

3-phenyl-1-propylmagnesium bromide

3-Phenyl-1-propylmagnesium bromide

→

alcohol

Yield 88.8%

1,7-Diphenyl-4-heptanol

Yield 88.8%

Solvents

THF

Conditions

Workup

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

Procedure

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.

Source