Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methanesulfonate | HCID 85257 | — |
| Reactant | Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester | HCID 3084696 | — |
| Reactant | 2-(2-Fluoro-phenoxy)-ethanol | HCID 21890808 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 53850434 | HCID 53850434 | 62.5% |
Reaction Steps
A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and treated with the mesylate of 2-(2-fiuorophenoxy)ethanol (1.17 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The dichloromethane extract was evaporated and the residue was purified by HPLC (dichloromethane-hexane; 4:1) and the resulting solids were crystallized from dichloromethane-diethyl ether to give 0.8 g of 4-[[2-(2-fiuorophenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 112°-113° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05344843 |
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| Source dataset | uspto-grants-1994_09 |
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| ORD ID | ord-c082f6fba0694a2a9fd47b9ee0349a2c |
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| Source note | uspto-grants-1994_09 |
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