Sodium hydride → HCID 22235805, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. suspension of unpurified 1,1-dimethyl-2-oxo-2-phenylethyl 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetate (4.4 g) in DMF (40 mL) was added a suspension of NaH (1.0 g of 60% dispersion, washed with hexanes) in DMF (10 mL). The mixture was stirred at 0° C. for 2 h, then diluted with EtOAc/ether (1:1) and 1 M HCl. The layers were separated and the organic phase was washed with water and brine, dried over MgSO4 and concentrated. The residue was dissolved in toluene (50 mL), treated with PPTS (100 mg) and heated to reflux with a Dean-Stark trap for 3 h. The solution was cooled, diluted with EtOAc (100 mL) and washed with water and brine. The organic phase was dried over MgSO4 and concentrated. Purification by flash chromatography (30–50% EtOAc/hexanes) provided 2-(5,5-dimethyl-2-oxo-4-phenyl-2,5-dihydro-3-furanyl)-1H-isoindole-1,3(2H)-dione, and 3-amino-5,5-dimethyl-4-phenyl-2(5H)-furanone.

Provenance & Evidence