Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methanesulfonate | HCID 85257 | — |
| Reactant | 2-naphthalen-2-ylsulfanylethanol | HCID 305520 | — |
| Reactant | Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester | HCID 3084696 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 54560109 | HCID 54560109 | 37.3% |
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-naphthylthio)ethanol (1.4 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 4:1) and crystallized from diethyl ether-hexane to provide 0.55 g of 4-[[2-(2-naphthalenylthio) ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 63°-65° 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-ea628da35b77405cbbb01a9acf93f5a9 |
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| Source note | uspto-grants-1994_09 |
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