Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | HCID 18680890 | HCID 18680890 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22620335 | HCID 22620335 | 79.2% |
Reaction Steps
Tetrahydrofuran (20 ml) solution of 1-(biphenyl-4-ylmethyl)-6-ethoxycarbonyl-2-methylbenzimidazole (5.30 g) is slowly added to a tetrahydrofuran (20 ml) solution of aluminum lithium hydride (2.17 g). Further, the solution is stirred for one hour at room temperature. By adding tetrahydrofuran (30 ml), the reaction solution is diluted. By adding a saturated sodium sulfate aqueous solution, the aluminum lithium hydride is decomposed, solidified and the tetrahydrofuran layer is separated. The solvent is removed through evaporation. Purification using silica gel column chromatography produced 1-(biphenyl-4-ylmethyl)-6-hydroxymethyl-2-methylbenzimidazole (3.72 g). 1H-NMR (CDCl3, δ): 2.59 (3H, s), 4.78 (2H, s), 5.37 (2H. s), 7.11 (2H, d, J=8.3 Hz), 7.24 (1H, d, J=8.3 Hz), 7.30-7.37 (2H, m), 7.42 (2H, t), 7.51-7.56 (4H, m), 7.70 (1H, d, J=8.2 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06369092B1 |
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| Source dataset | uspto-grants-2002_04 |
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| ORD ID | ord-78a86ff9eafc4b68b395cbbddde028d8 |
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| Source note | uspto-grants-2002_04 |
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