Methanol → HCID 66590129, compound

Participants

Reaction Steps

Into a 100 mL round bottom flask was added 4E and toluene (42 mL) under nitrogen. Sodium metal (392 mg, 17.1 mmol, 1.3 eq) was added at once followed by methanol (160 μL, 3.9 mmol, 0.3 eq). The reaction was allowed to stir under nitrogen over 48 hours. After sodium metal had dissolved, saturated ammonium chloride (50 mL) was added to quench the reaction. Ethyl acetate (50 mL) was added and the mixture was transferred to a separatory funnel. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (2×50 mL). The organic layers were combined and dried over sodium sulfate and filtered. Solvent was removed under vacuum to leave a residue which was purified by column chromatography (20% ethyl acetate/hexanes) to give 4F (4.17 g, 62%). ESI-MS:m/z 459.3 (M+H)+.

Provenance & Evidence