Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Ethyl 4-methylpentanoate | HCID 117477 | — |
| Reactant | lithium aluminium hydride THF | HCID 68718528 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 12598593 | HCID 12598593 | 42% |
Reaction Steps
Under a nitrogen atmosphere, ethyl 4-methylpentanoate (350 mg) was dissolved in tetrahydrofuran (10 mL) at −78° C., a lithium aluminum hydride/tetrahydrofuran solution (1.0 M, 1.58 mL) was added, and the mixture was stirred. While the temperature of the mixture was naturally returned to room temperature, the mixture was stirred, and after 1.5 hours, water (0.05 mL), a 2N aqueous sodium hydroxide (0.05 mL) and water (0.15 mL) were successively added thereto, and the mixture was stirred. Further, diethyl ether was added thereto, and then the resulting insoluble matters were filtered off and the filtrate was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate system), to give the title compound as a colorless oil (257 mg, 42%: 2 steps).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06906072B1 |
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| Source dataset | uspto-grants-2005_06 |
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| ORD ID | ord-cb47566cf49245fb83e68747abce4840 |
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| Source note | uspto-grants-2005_06 |
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