Diisobutylaluminum hydride → 5-(Hydroxymethyl)-1H-benzimidazole

To a cooled (0° C.) suspension of ethyl-benzimidazole-5-carboxylate (4.76 g, 25 mmol) in CH2Cl2 (100 mL) was added a 1 M solution of DIBAL in CH2Cl2 (100 mL) and the mixture was stirred for 4 h. The reaction was quenched by the sequential addition of MeOH (8 mL), 1M NaOH (16 mL), and 30% sodium potassium tartrate (40 mL). The mixture was warmed to RT and filtered, and the solid residue was washed with CH2Cl2. The filtrate was concentrated in vacuo to afford the title compound as a brown solid: 1H NMR (400 MHz, DMSO-d6): δ4.58 (s, 1H), 7.14 (m, 1H), 7.46 (s, 1H), 7.51 (m, 1H), 8.15 (s, 1H); HRMS (FAB) C8H9N2O calcd. 149.1723 (M+1). Found 149.1045.

1. temperatureTo a cooled
2. customThe reaction was quenched by the sequential addition of MeOH (8 mL), 1M NaOH (16 mL), and 30% sodium potassium tartrate (40 mL)
3. filtrationfiltered
4. washthe solid residue was washed with CH2Cl2
5. concentrationThe filtrate was concentrated in vacuo

ORDレコード

ord-2b7aeb2f4d7f40889c0149c021f90d69

出典データセット

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06610701B2