Ethyl formate → HCID 67468834, compound

Participants

Reaction Conditions

Reaction Steps

NaH (57 mg, 1.4 mmol) was added in small portions to a mixture of 1′-(4-tert-butyl-3-methoxy-benzoyl)spiro[chromane-2,4′-piperidine]-4-one (250 mg, 0.61 mmol) in THF (2.5 mL) at 25° C. A solution of ethyl formate (74 μL, 0.90 mmol) in THF (0.5 mL) was added and the mixture was allowed to stir at 25° C. for 3 h before it was quenched with 0.5M aqueous HCl. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over sodium sulfate, and concentrated in vacuo to provide 1′-(4-tert-butyl-3-methoxybenzoyl)-3-(hydroxymethylene)spiro[chroman-2,4′-piperidin]-4-one (50 mg, 19%) as an orange oil. ESI-MS m/z talc. 435.2, found 436.2 (M+1)+; Retention time: 1.87 minutes (3 min run).

Provenance & Evidence