Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (4,4-Difluorocyclohexyl)methanol | HCID 21184133 | — |
| Reactant | HCID 90416744 | HCID 90416744 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 90416509 | HCID 90416509 | 83% |
Reaction Steps
A solution of (4,4-difluorocyclohexyl)methanol (0.156 g, 1.04 mmol) in anhydrous tetrahydrofuran (4.33 mL) under nitrogen was treated with sodium hydride (0.042 g, 1.040 mmol) at ambient temperature, stirred for 10 minutes, treated with the product from Example 17C (0.087 g, 0.26 mmol) and heated under nitrogen at 60° C. for 18 hours. The mixture was cooled and partitioned into ethyl acetate/water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-60% ethyl acetate in heptanes) afforded the title compound (0.1 g, 83%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09321764B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-b235236f591040ad9765bad099ecec6f |
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| Source note | uspto-grants-2016_04 |
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