Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | HCID 15724967 | HCID 15724967 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 15725027 | HCID 15725027 | 71% |
Reaction Steps
To a solution (5 ml) of 2-(1H-indol-2-yl)thio-2-phenylpropionic acid (1.5 g) and diethyl azodicarboxylate (0.96 g) in anhydrous tetrahydrofuran, a solution (5 ml) of benzyl alcohol (0.81 g) and triphenylphoshine (1.44 g) in anhydrous tetrahydrofuran was added dropwise under an argon atmosphere, and the mixture was stirred at room temperature overnight. The solvent was evaporated off under reduced pressure. Benzene was added to the residue, and deposited crystalline matter was filtered and the solvent was evaporated. The residue was purified by silica gel column chromatography (diluting solvent: n-hexane/ethyl acetate=9:1), and was further recrystallized from ethyl acetate/n-hexane to give 1.37 g (yield 71 %) of the product compound as a colorless scale-like crystal. The melting point was 102°-103° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05137909 |
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| Source dataset | uspto-grants-1992_08 |
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| ORD ID | ord-d4b11bd418b743d8893744335ad63d8a |
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| Source note | uspto-grants-1992_08 |
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