Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | HCID 54307398 | HCID 54307398 | — |
| Catalyst | Acetone | HCID 180 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 18347204 | HCID 18347204 | — |
Reaction Steps
To a solution of 3-cyanomethyl-4-(4-(methylthio)phenyl)-5-phenylthiophene-2-carboxylic acid methyl ester (480 mg) (Step 1) in THF (13 mL) was added 55 mg of LiBH4 followed by 50 μL of MeOH; then the mixture was heated at 50° C. for 90 min. After cooling to r.t. a few drops of acetone were slowly added, then a saturated solution of NH4Cl. The mixture was then extracted twice with EtOAc, the organic layers combined, washed with brine, dried over MgSO4, filtered and the solvent evaporated under vacuum. Purification by silica gel chromatography using 30% of EtOAc in hexane afforded the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05521213 |
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| Source dataset | uspto-grants-1996_05 |
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| ORD ID | ord-1979d52ebf064051a7ec12a974a9d5bb |
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| Source note | uspto-grants-1996_05 |
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