Sodium Hydroxide → HCID 22500388, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of the product of step b (1.00 g, 3.27 mmol) in THF (10 ml) was added dropwise a solution of lithium aluminium hydride (1M, THF, 3.50 ml, 3.50 mmol) and the mixture was stirred at this temperature for 3 h. The reaction mixture was treated sequentially with water (0.14 ml), aqueous sodium hydroxide (2M, 0.14 ml) and water (0.42 ml) and allowed to warm to ambient temperature. Sodium sulfate was added and the resultant suspension filtered through a pad of celite and the filter-cake washed with further ethyl acetate (150 ml). The filtrate was evaporated at reduced pressure and the residue purified by flash column chromatography (3:1 ethyl acetate:hexane) to afford the title compound (524 mg, 61%). 1H NMR 8.50 (1H, s), 8.04-7.86 (4H, m), 7.72-7.63 (2H, m), 3.66-3.62 (2H, m), 3.27-3.21 (2H, m), 1.91-1.83 (2H, m), 1.71-1.65 (2H, m), 1.56 (1H, br s).

Provenance & Evidence