Reaktion #975

Reaktionsgleichung

4-phenyl-1-butanal

4-Phenyl-1-butanal

3-phenyl-1-propylmagnesium bromide

3-Phenyl-1-propylmagnesium bromide

→

alcohol

Ausbeute 88.8%

1,7-Diphenyl-4-heptanol

Ausbeute 88.8%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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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