Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-(Chloromethoxy)-2-methoxyethane | HCID 77590 | — |
| Reactant | HCID 69307856 | HCID 69307856 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 69306558 | HCID 69306558 | 64% |
Reaction Steps
Methyl 2-{4-[(4-fluorobenzyl)oxy]phenyl}-2-hydroxyacetate (0.507 g, 1.75 mmol) was dissolved in tetrahydrofuran (9 ml), and sodium hydride (0.09 g, 2.27 mmol) was added thereto while being cooled with ice. The mixture was stirred for 30 minutes at room temperature, and 2-methoxyethoxymethylchloride (0.26 ml, 2.27 mmol) was added thereto while being cooled with ice. After being stirred for 62 hours at room temperature, the mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was dried over MgSO4, and then the solvent was evaporated out. The obtained residue was purified by silica gel column chromatography (30% ethyl acetate/hexane), to give methyl 2-{4-[(4-fluorobenzyl)oxy]phenyl}-2-[(2-methoxyethoxy)methoxy]acetate (0.421 g, 64%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07348017B2 |
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| Source dataset | uspto-grants-2008_03 |
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| ORD ID | ord-81e242eb6daf4ea4b4c664d7a1a62ada |
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| Source note | uspto-grants-2008_03 |
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