Towards a Scalable Synthesis of 2‐Oxabicyclo[2.2.0]hex‐5‐en‐3‐one Using Flow Photochemistry

Cyclobutene lactones hold great potential as synthetic building blocks, yet their preparation by photochemical rearrangement in batch can often be a bottleneck in synthetic studies. We report the use of flow photochemistry as a tool to enable a higher‐throughput approach to the synthesis of 2‐oxabicyclo[2.2.0]hex‐5‐en‐3‐one, which reduces reaction times from 24 hours to 10 minutes. Accordingly, a significantly improved throughput of 144 mg/h (vs 14‐21 mg/h in batch) was achieved. Scale‐out experiments showed problematic reactor fouling, whereby steps were taken to explore and minimize this effect.

• Jason D. Williams^a,b
• Yuma Otake^a
• Guilhem Coussanes^c
• Iakovos Saridakisc^c
• Nuno Maulidec^c
• C. Oliver Kappea^a,b

• ^a Center for Continuous Flow Synthesis and Processing (CC FLOW), Research Center Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010 Graz, Austria
• ^b Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, 8010 Graz, Austria
• ^c Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090 Vienna, Austria

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