反应详情

温度

50 °C

To a 5-L, round-bottom flask fitted with a stir bar and a Claisen adapter fitted with a thermocouple and a nitrogen line was added was added methyl 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)benzoate (40.5 g, Step B) tetrahydrofuran (1.25 L), methanol (630 ml), water (315 ml), and lithium hydroxide monohydrate (10.7 g). The mixture was heated to 50° C. and stirred at this temperature for 1 h. The mixture was then cooled and concentrated to a thick slurry. 1N HCl (3.2 L) was added and an off-white solid formed. The mixture was stirred for 5 min and then filtered, washing with water (2×500 ml). The solid was transferred to a 2-L round-bottom flask, concentrated from toluene (1 L) and then dried in vacuo. Mass spectrum (ESI) 307.0 (M+1). 1H NMR (500 MHz, DMSO-d6): δ 8.69 (d, J=7.5 Hz, 2H), 8.28 (s, 1H), 8.16 (d, J=8.0 Hz, 2H), 7.81 (s, 1H), 3.46 (septet, J=6.5 Hz, 1H), 1.40 (d, H=7.0 Hz, 6H).

1. customa Claisen adapter fitted with a thermocouple
2. additiona nitrogen line was added
3. temperatureThe mixture was then cooled
4. concentrationconcentrated to a thick slurry
5. addition1N HCl (3.2 L) was added
6. customan off-white solid formed
7. stirringThe mixture was stirred for 5 min
8. filtrationfiltered
9. washwashing with water (2×500 ml)
10. customThe solid was transferred to a 2-L round-bottom flask
11. concentrationconcentrated from toluene (1 L)
12. customdried in vacuo