Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydroxylamine | HCID 787 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | Tetrahydro-2H-pyran-4-carboxaldehyde | HCID 9964078 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 76979141 | HCID 76979141 | 50.2% |
Reaction Steps
To a suspension of tetrahydro-pyran-4-carbaldehyde (36.9 g, 259 mmol) and hydroxylamine (27.2 g, 388 mmol) in ethanol (246 mL) and water (246 mL) was added sodium acetate (42.9 g, 517 mmol) and the resulting mixture heated at 90° C. overnight. After cooling to room temperature the resulting mixture was then evaporated and extracted with diethylether and water. The organic extract was then washed with water, brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=1:1) afforded the title compound (16.8 g, 50%) which was obtained as a yellow liquid. MS: m/e=129.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163728B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-311d8929f7774c16abb6b78640db8167 |
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| Source note | uspto-grants-2012_04 |
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