HCID 15686893, compound → HCID 21904693, compound

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).

1. custombefore being quenched cautiously by the addition of water (1.4 mL)
2. additionExcess MgSO4 was then added
3. customformed (ca. 5 mL)
4. filtrationThe mixture was then filtered
5. customevaporated to a brown oil (7.1 g, ca. 95%)
6. customIt was used directly in the next stage without further purification

ORD record

ord-4dce28c6ff90420d9337d939612ca557

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129234B2