Diisopropyl diazene-1,2-dicarboxylate → HCID 67538659, compound

Participants

Reaction Steps

20 g of ascorbic acid (113.5 mmol; 1 eq.) are dissolved in 100 ml of di-methylformamide in an argon-flushed 3-necked flask, 32.76 g of triphenyl-phosphine are added, and 25.3 g of diisopropyl azodicarboxylate (124.9 mmol; 1.1 eq) are slowly added dropwise at 0° C. After 30 min, the 2-ethylhexyl(E)-3-(4-hydroxyphenyl)acrylate (32.95 g; 1.05 eq; 119.2 mmol) dissolved in 45 ml of dimethylformamide is added dropwise. After 30 min at 0° C., the mixture is stirred at room temperature for a further 6 hrs. The reaction solution is evaporated to dryness, suspended in 100 ml of ethyl acetate/hexane 1:2, filtered, and the product is precipitated as a white solid by addition of 100 ml of hexane.

Provenance & Evidence