Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 18794887 | HCID 18794887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Lithium tri-s-butylborohydride | HCID 3611392 | — |
| Product | HCID 86755321 | HCID 86755321 | 72.5% |
Reaction Steps
To 2.26 g of tert-butyl 2-{5-(ethoxycarbonyl)-2-furylmethyl}-3-oxobutanoate in 50 ml of tetrahydrofuran, 7.7 ml of 1M lithium tri-sec-butylborohydride in tetrahydrofuran solution was added at -78° C. under stirring, and the resulting reaction solution was stirred at the same temperature for 2 hours. After addition of water, the reaction solution was stirred at room temperature for 30 minutes and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=12/1→4/1] to give 1.65 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06048894 |
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| Source dataset | uspto-grants-2000_04 |
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| ORD ID | ord-6b27b8236fb34940a2cb334dfc39720c |
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| Source note | uspto-grants-2000_04 |
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