Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | HCID 19382375 | HCID 19382375 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 19382364 | HCID 19382364 | — |
Reaction Steps
2-Pivaloyl-3-furoic acid (1.96 g, 0.01 mol) was dissolved in acetone (40 ml) and the solution was stirred at 0° C. under nitrogen. Triethylamine (1.7 ml, 0.012 mol) was added, followed by ethyl chloroformate (1.24 ml, 0.013 mol) and the mixture was stirred for 11/2 hours. A solution of sodium azide (1.11 g, 0.017 mol) in water (4 ml) was added and the suspension was stirred for another 2 hours at 0° C. The solid was removed by filtration and the filtrate was diluted with water (25 ml). It was concentrated in vacuo to remove the acetone. The oil-water residue was extracted with ethyl acetate. The ethyl acetate extract was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated to an amber oil (2.06 g) of 87% purity by HPLC.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05453424 |
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| Source dataset | uspto-grants-1995_09 |
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| ORD ID | ord-54709f26c0f94a4d820d586cd2d6e99e |
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| Source note | uspto-grants-1995_09 |
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