Methanol → HCID 54260281, compound

Participants

Reaction Conditions

Reaction Steps

Under a current of argon, a solution of 710 mg of methyl 4-methoxymethoxy-3-nitrocinnamate in 6 ml of toluene and 4.4 ml of diisobutyl aluminum hydride (1.5M toluene solution) added thereto at -78° C. were stirred for 30 minutes. The produced reaction solution was combined with methanol at -78° C. to effect decomposition of excess diisobutyl aluminum hydride and then the resultant mixture and water added thereto at 0° C. were stirred for a while. Subsequently, the mixture was filtered with sellaite and wased with ethyl acetate and the filtrate was extracted from ethyl acetate. The consequently separated organic layer was washed with saturated saline solution and then with anhydrous sodium sulfate and concentrated under a vacuum. The resultant concentrate was subjected to silica gel column chromatography. From the hexane-ethyl acetate (1:1 V/V) eluate, 560 mg of 4-methoxymethoxy-3-nitrocinnamyl alcohol was obtained in the form of a yellow oily substance. The yield was 88%.

Provenance & Evidence