Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclopentanol | HCID 7298 | — |
| Reactant | 4-Fluorobenzonitrile | HCID 14517 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 24690142 | HCID 24690142 | 80.1% |
Reaction Steps
Suspend sodium hydride (336 mg, 2.8 mmol, 60% suspension in mineral oil) in anhydrous 1,4-dioxane (10 mL) under nitrogen atmosphere. Add cyclopentanol (620 mg, 7.2 mmol) and stir the resulting solution for 30 min. Add the preformed solution (3.35 mL, 2.4 mmol) to neat 4-fluorobenzonitrile (240 mg, 2 mmol) in a microwave tube and heat the sealed mixture at 100° C. for 30 min. Cool to room temperature and concentrate in vacuo. Purify by chromatography on silica gel eluting with isohexane/EtOAc (95:5 to 1:1 gradient) to obtain the desired intermediate (300 mg, 80%). GC-MS m/z: 187 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08580780B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-0bebb288cc0a45e4ae5260b4b16f910c |
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| Source note | uspto-grants-2013_11 |
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