Ethanol → HCID 86731081, compound

Participants

Reaction Steps

1-Methylindoline-2,3-dione (5.0 g, 31.0 mmol) was stirred in DMF (15 mL) and Ethanol (85 mL) at 0° C. Ethyl 2-diazoacetate (4.51 mL, 43.4 mmol) was added. The ice bath was removed and the mixture was stirred at rt for two days. The mixture was evaporated to remove most of the EtOH. 1N HCl (ca. 100 mL) was added. It was stirred at rt for 3 h. LC-MS showed the desired ring expansion product. The precipitate was filtered and rinsed with H2O (2×) and dried under vacuum to give Intermediate 16 (5.05 g, 20.42 mmol, 94% yield) as slightly tan solids. LC-MS (ESI) 248.0 (M+H), RT=2.91 min (Method A).

Provenance & Evidence