Reaktion #483305

Reaktionsgleichung

hydrochloric acid

isopropenylmagnesium bromide

5-benzyloxy-2-nitrobenzaldehyde

water

→

1-[5-(benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol

Ausbeute 48.7%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   Temperaturwarmed to room temperature
3. 3
   Extraktionthe aqueous phase is extracted 2× with ethyl acetate
4. 4
   Trocknenthe combined organic extracts are dried over sodium sulphate
5. 5
   SonstigePurification of the crude product on silica gel (CH2Cl2)

Vorschrift

35.9 ml (16.33 mmol) of a 0.5 M isopropenylmagnesium bromide solution in THF are slowly added at −78° C. to a solution of 3.0 g (11.66 mmol) of 5-benzyloxy-2-nitrobenzaldehyde in 50 ml of THF. After addition is complete, the mixture is stirred at −78° C. for 2 h, then treated with 40 ml of water and warmed to room temperature. The mixture is treated with 10 ml of 1 N hydrochloric acid, the aqueous phase is extracted 2× with ethyl acetate, and the combined organic extracts are dried over sodium sulphate and freed from the solvent in vacuo. Purification of the crude product on silica gel (CH2Cl2) affords 1.7 g (48.7%) of 1-[5-(benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol as a yellow oil.

Quelle