Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diethyl azodicarboxylate | HCID 5462977 | — |
| Reactant | HCID 136414661 | HCID 136414661 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 135736093 | HCID 135736093 | 24.4% |
Reaction Steps
Diethylazodicarboxylate (0.92 g, 1.7 eq) in THF (20 ml) was added to a mixture of 1-adamantyl (2-chloro-4,6-dihydroxyphenyl)methanone oxime (1 g, 3.1 mmoles), triphenyl phosphine (1.4 g, 1.7 eq) in THF (20 ml) at 0° C. The mixture was stirred 2 h at 0° C., poured into water, extracted with ethylacetate, dried over Na2SO4 and concentrated under vacuum to give the crude product. Flash chromatography (AcOEt/toluene 1/9) and crystallisation from EtOH yielded the expected product (230 mg, 23%). mp 215° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08173679B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-ab484ee713e64dc89ab9264414ad7391 |
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| Source note | uspto-grants-2012_05 |
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