Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Malonate | HCID 7761 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 21866742 | HCID 21866742 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 69590757 | HCID 69590757 | 82.2% |
Reaction Steps
To 15 ml of dry tetrahydrofuran and 7 ml of dry N,N-dimethylformamide, 0.88 g of 60% sodium hydride was added. To the mixture was added dropwise 4.40 g of diethyl malonate with stirring under ice-cooling. After 15-minute-stirring, a solution of 3.93 g of 3-{[5-methyl-2-(p-tolyl)oxazol-4-yl]methyl}benzyl bromide/5 ml of dry tetrahydrofuran was added and stirred for 1 hour under ice-cooling. The reaction solution was poured into ice-cold water, extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=5:1) to provide 3.95 g of the objective compound as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07022723B2 |
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| Source dataset | uspto-grants-2006_04 |
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| ORD ID | ord-56eccdec02a7452c81202b01f1583602 |
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| Source note | uspto-grants-2006_04 |
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