Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methanesulfonate | HCID 85257 | — |
| Reactant | 2-(4-Nitrophenoxy)ethanol | HCID 85381 | — |
| Reactant | Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester | HCID 3084696 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 54388349 | HCID 54388349 | 54% |
Reaction Steps
A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylforrnamide (10 mL) under argon was treated with 55% sodium hydride (0. 175 g), stirred for 15 minutes and treated with the mesylate of 2-(4-nitrophenoxy)ethanol (1.56 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material was purified by HPLC (dichloromethane-hexane; 9:1) and crystallized from dichloromethane-hexane to provide 0.75 g of 4-[[2-(4-nitrophenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester as a 4:1 molar hydrate, mp 122°-123° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05344843 |
|---|
| Source dataset | uspto-grants-1994_09 |
|---|
| ORD ID | ord-aef0e4c504e0407f8c242cce8fef52f3 |
|---|
| Source note | uspto-grants-1994_09 |
|---|