Tetrahydrofuran → HCID 178519339, compound

1H-benzo[d]imidazole-5-carboxylic acid (5.39 g, 33.3 mmol) was dissolved into anhydrous THF (100 ml) under argon. The solution was cooled in an ice bath and lithium aluminum hydride (70.0 ml of 1M solution in THF, 70.0 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and stir overnight. The reaction mixture was cooled to 0° C. and ethyl acetate (90 ml) was carefully added, followed by methanol (15 ml) and water (15 ml). The mixture was stirred for 1 h and filtered through celite. The Solution was concentrated and dissolved in THF (200 ml) and washed with brine (2×100 ml), dried over Na2SO4, filtered and concentrated to yield the title compound ((1H-benzo[d]imidazol-5-yl)methanol) (1.26 g, 26%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.15 (s, 1H), 7.54-7.47 (m, 2H), 7.13 (s, 1H), 5.14 (s, 1H), 4.58 (s, 2H).

1. temperatureThe solution was cooled in an ice bath
2. temperatureThe reaction mixture was cooled to 0° C.
3. stirringThe mixture was stirred for 1 h
4. filtrationfiltered through celite
5. concentrationThe Solution was concentrated
6. dissolutiondissolved in THF (200 ml)
7. washwashed with brine (2×100 ml)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-98c69ee796cc44dcac483f4fff60699e

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2