Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,4-Dibromobutane | HCID 8056 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate | HCID 57995474 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57995609 | HCID 57995609 | 102.5% |
Reaction Steps
Ethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetate (0.5 g) was dissolved in 10 mL anhydrous DMF and NaH (60% wt. in oil, 0.13 g, mmol) was added at 0° C. The reaction mixture was stirred for 0.5 h at 25° C. and 1,4-dibromobutane (0.24 g, mmol) was added drop wise at 0° C. The reaction mixture was stirred at 0° C. for 1 h and saturated NH4Cl solution (10 mL) was added. The reaction mixture was extracted with EtOAc (3×20 mL) and the combined organic phases were washed with water (3×20 mL) and brine (20 mL), and dried over MgSO4, filtered and concentrated under reduced pressure to give ethyl 1-(3-(cyclopropylmethoxy)-4-nitrophenyl)cyclopentanecarboxylate (380 mg) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08664249B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-c72820b9e9384ffe8ae78cbe227fc156 |
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| Source note | uspto-grants-2014_03 |
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