Hydrochloric Acid → HCID 86721376, compound

Participants

Reaction Conditions

Reaction Steps

[step 5] Propyl 11-(1-cyanoethylidene)-3-fluoro-6,11-dihydrodibenzo[b,e]oxepin-8-carboxylate (15.5 g, 44.1 mmol, E/Z=1/1) obtained in step 4 was dissolved in THF (220 mL), lithium borohydride (4.8 g, 221 mmol) was added, and the mixture was stirred at 60° C. for 3 hr. Under ice-cooling, the mixture was added dropwise to 2 mol/L hydrochloric acid, and the mixture was extracted 3 times with chloroform (550 mL). The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified 3 times by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-40/60 v/v) to give (E)-2-[3-fluoro-8-(hydroxymethyl)dibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (6.06 g, 47%).

Provenance & Evidence