Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ethyl 6-bromohexanoate | HCID 117544 | — |
| Reactant | HCID 54929897 | HCID 54929897 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86663480 | HCID 86663480 | 45.4% |
Reaction Steps
The compound (480 mg, 1.86 mmol) obtained in Example 99a was dissolved in N,N-dimethylformamide (6 mL), 55% sodium hydride (89 mg, 2.79 mmol) was added under ice cooling, and the mixture was stirred at the same temperature under a nitrogen atmosphere for 20 minutes. Subsequently, ethyl 6-bromohexanoate (623 mg, 2.79 mmol) was added, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, water was added, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:3, v/v) to give the title compound (338 mg; yield, 45%) as a pale orange color oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08476253B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-0aff4429e5d44e42b18f58963590ccdf |
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| Source note | uspto-grants-2013_07 |
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