Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 57864405 | HCID 57864405 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57864412 | HCID 57864412 | — |
Reaction Steps
3.50 g (10.3 mmol) of 5-fluoro-2-[3-(4-trifluoromethylphenyl)prop-2-ynyloxy]benzoic acid are suspended in 10 ml of THF, 1.04 g (10.3 mmol) of N-methylmorpholine are added, the mixture cooled to 0° C., and 1.12 g (10.3 mmol) of ethyl chloroformate are added. The mixture is warmed to room temperature and stirred for 30 min. 1.17 g (31.0 mmol) of sodium borohydride are added to this solution, and the mixture is stirred at room temperature for 5 h. Then methanol is added until gas evolution has subsided, and subsequently 1 N hydrochloric acid is used to acidify. The solvent is distilled out in vacuo, and the residue is taken up in ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried over sodium sulfate, and the solvent is distilled out in vacuo. 4.62 g (8.69 mmol, 85% of theory) of the title compound are isolated.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07998988B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-ec7ed8702966488fbdd1da72fd211d1c |
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| Source note | uspto-grants-2011_08 |
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