Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-Methyloxybenzyl chloride | HCID 69993 | — |
| Reactant | HCID 3343465 | HCID 3343465 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58424909 | HCID 58424909 | 84% |
Reaction Steps
N,N-Dimethylformamide was added to the compound (972.4 mg, 3.1736 mmol) prepared in step 1 and the mixture was cooled to 0° C. Sodium hydride (380 mg, 9.52 mmol) was slowly added and the resulting mixture stirred at 0° C. for 20 minutes. p-Methoxybenzyl chloride (0.646 ml, 4.76 mmol) was added at 0° C. and the mixture stirred for 3 hours at room temperature. Once the reaction was completed, dichloromethane and water was added, the organic layer was dried over magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=2.5:1) to obtain the title compound (1.01 g, yield: 84%, ivory oil).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08815891B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-bf969fd664d94990925c72c39e13b68a |
|---|
| Source note | uspto-grants-2014_08 |
|---|