HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 58292591, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Chloro-4-nitropyridine 1-oxide | HCID 84433 | — |
| Reactant | Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate | HCID 58292549 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58292591 | HCID 58292591 | 29% |
Reaction Steps
(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (2 g, 8 mmol), 2-chloro-4-nitro-pyridine oxide (2.2 g, 12 mmol) and Cs2CO3 (5.7 g, 18 mmol) were mixed in DMF (50 mL) and stirred at room temperature for 1 h. Water was added and the reaction mixture was adjusted to pH 3. The reaction mixture was extracted with ethyl acetate. The organic layers were concentrated to give a residue. The residue was purified by flash column chromatography (dichloromethane:methanol=15:1) to give the title compound (0.77 g, 29%) as a brown solid. MS found (electrospray): (M+H)+=389.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08343944B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-dff1f47aad6344ce84df5e44fb5e0920 |
| Source note | uspto-grants-2013_01 |