Sodium t-butoxide → HCID 68839471, compound

Participants

Reaction Steps

A solution of the product from Step 4 (0.50 g, 1.24 mmol) in N,N-dimethylformamide (3.0 mL) was cooled to 0° C. and sodium tert-butoxide (0.24 g, 2.54 mol) was added. The reaction was stirred and warmed to room temperature over 1.5 hours. The reaction was quenched by the addition of ice (50 g) and the resulting mixture was diluted with H2O (20 mL), methyl tert-butyl ether (30 mL) and ethyl acetate (100 mL). The organic layer was separated, washed with a 2% lithium chloride solution (20 mL) and then saturated sodium chloride solution (20 mL). The organic layer was dried over sodium sulfate and concentrated to afford a solid that was triturated with a 1:1 cyclohexan/heptane mixture to provide 0.31 g (68%) of the product as a light-yellow solid. 1H NMR (400 MHz, Methanol-d4) δ 7.38-7.18 (m, 5H), 4.87-4.51 (m, 1H), 4.22-4.11 (m, 1H), 3.94-3.48 (m, 4H), 3.59 (s, 3H), 3.22-3.07 (m, 1H), 2.78-2.64 (m, 2H), 2.61-2.43 (m, 2H), 2.40-2.13 (m, 3H). MS 368.2 (AP+, 100).

Provenance & Evidence