HuagongsheHuagongshe Chemistry Print Report · For research reference only
3,4-dihydro-2H-pyran → 1-(Tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- | HCID 18462 | — |
| Reactant | HCID 178524171 | HCID 178524171 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(Tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylic acid | HCID 71272493 | 60% |
Reaction Steps
To the solution of 1H-benzoimidazole-5-carboxylic acid (1.62 g, 10 mmol) in THF (20 mL) was added 3,4-dihydro-2H-pyran (2 mL) and camphorsulfonic acid (100 mg, 0.42 mmol, 0.04 equiv). The mixture was refluxed for 24 h under argon. Concentration and chromatography afforded 1.5 g (60%) of 1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carboxylic acid (166) as a light red solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637537B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-7e715e7f64ca4de9b17816c1007d03c8 |
| Source note | uspto-grants-2014_01 |