Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2,3-Dihydroxybenzonitrile | HCID 3017820 | — |
| Reactant | HCID 11076628 | HCID 11076628 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 58506482 | HCID 58506482 | 34.7% |
Reaction Steps
To a solution of 2,3-dihydroxybenzonitrile (13.5 g, 1 eq.) in DMSO (200 mL) was added NaH (60%, 8 g, 2eq.) and the resulting solution was stirred for 1 h at 60° C. 2-(2-Methoxyethoxy)ethyl 4-methylbenzenesulfonate (20 g, 0.7eq.) in DMSO (100 mL) was added dropwise at 60° C. and stirring was continued for another 1 h. The reaction was quenched by NH4Cl (sat.), the mixture was extracted with EtOAc (300 mL×3) and the combined organic layers were dried over Na2SO4. The solvent was evaporated and the residue was purified by silicon column (EtOAc/PE=1/1) to give the title compound (6 g, 25%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09045440B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-936ad2804655424898594371297763c0 |
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| Source note | uspto-grants-2015_06 |
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