Hydrochloric Acid → (Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of the ester from Step 1 (3.39 g, 9.57 mmol) in toluene (75 mL) at −70° C., there was slowly added diisobutyl aluminum hydride (1M) in toluene (12 mL, 12 mmol) and the resulting mixture stirred at −70° C. for 45 minutes. Methanol (10 mL) was added slowly at −70° C., then the mixture was warmed to room temperature and water (100 mL) and 1N aqueous HCl (50 mL) were added. The mixture was shaken and the organic layer collected; the aqueous fraction was extracted with ether and the combined organic fractions washed 3 times with water, dried over MgSO4 and evaporated down to a thick oil. The crude title compound was used as such in the next step.

Provenance & Evidence