Sodium hydride → HCID 58288703, compound

Participants

Reaction Steps

To a round-bottom flask is charged naphthalene-1,8-diol (4.0 g, 25 mmol), and anhydrous DMF (50 ml). The flask is immersed in an ice-water bath, and 60% sodium hydride in mineral oil (2.4 g, 60 mmol) is added in portions. The mixture is stirred for an hour. Isobutyl chloroformate (8.2 g, 60 mmol) is added dropwise. After gradually warming to room temperature, the mixture is stirred overnight. The mixture is poured into ice-cold water and extracted with ether three times. The combined ether extracts are washed with water, then brine, and then dried over magnesium sulfate. After filtration, the filtrate is concentrated, and the residue is purified by flash column chromatography on silica gel to yield 2.8 g (31%) of the product as a light-grey solid. 1H NMR (400 MHz, CDCl3, ppm) δ 7.79 (dd, 2H, J=1.2, 8.0 Hz), 7.47 (dd, 2H, J=7.6, 8.0 Hz), 7.26 (dd, 2H, J=1.2, 7.6 Hz), 4.07 (d, 4H, J=6.8 Hz), 2.07 (m, 2H), 1.00 (d, 12 H, J=6.8 Hz).

Provenance & Evidence