HCID 15686893, compound → HCID 21904693, compound

Participants

Reaction Steps

Dimethyl 4-(allyloxy)phthalate [prepared according to Inouye, M.; Tsuchiya, K.; Kitao, T. Angew. Chem. 1992, 104, 198-200 (See also Angew. Chem., Int. Ed. Engl, 1992, 204-205)] (9.9 g, 38 mmol) was dissolved in THF (40 mL) and cooled to 0° C. before the dropwise addition of lithium aluminium hydride (1M in THF, 77 mL, 77 mmol) over 10 min. The mixture was then allowed to stir at room temperature for 3 h before being quenched cautiously by the addition of water (1.4 mL) followed by 2M NaOH (1.4 mL). Excess MgSO4 was then added followed by water until a granular precipitate formed (ca. 5 mL). The mixture was then filtered and evaporated to a brown oil (7.1 g, ca. 95%). 1H NMR showed the material to be of ca. 85% purity. It was used directly in the next stage without further purification; δH (CDCl3, 400 MHz) 2.63 (1H, brs), 2.91 (1H, brs), 4.52 (2H, m), 4.67 (4H, m), 5.26 (1H, dd), 5.38 (1H, dd), 5.97-6.09 (1H, m), 6.80 (1H, dd), 6.92 (1H, d), 7.22 (1H, d).

Provenance & Evidence