Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 86694687 | HCID 86694687 | — |
| Reactant | HCID 178461630 | HCID 178461630 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 71272254 | HCID 71272254 | 72% |
Reaction Steps
A solution of EtMgBr (0.72 mL, 1 mol/L) was added to N-methoxy-N-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carboxamide (70 mg, 0.24 mmol) in THF at 0° C. under argon. The mixture was stirred at 0° C. for 2 h. A solution of NH4Cl was added, carefully, to quench the reaction. The mixture was poured into water and extracted with EtOAc. The organics were washed sequentially with water and brine, then dried (Na2SO4). Removal of solvent followed by SiO2 chromatography afforded 1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)propan-1-one as a colorless oil (45 mg, 72% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08637537B2 |
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| Source dataset | uspto-grants-2014_01 |
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| ORD ID | ord-33970f9dc0534989a06f64bb141167b7 |
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| Source note | uspto-grants-2014_01 |
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