Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Methyl 4-cyano-3-hydroxybenzoate | HCID 16641129 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 53919960 | HCID 53919960 | — |
Reaction Steps
4-cyano-3-hydroxybenzoic acid methyl ester, Example 34, Step 3 (2 g, 11.3 mmol) was dissolved in CH2Cl2 (57 ml) and cooled to 0° C. in an ice bath. The mixture was treated with Et3N (3 ml, 22.6 mmol) followed by the addition of Tf2O (1.9 ml, 11.3 mmol). The reaction mixture was warmed to room temp. and stirred for 4 hours. Saturated NaHCO3 (10 mL) was added and the mixture was extracted with EtOAc (2×10 mL). The organic layers were combined and dried (MgSO4), filtered, and concentrated. The residue was then purified by flash chromatography (15% EtOAc/Hexane) to yield the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06077853 |
|---|
| Source dataset | uspto-grants-2000_06 |
|---|
| ORD ID | ord-6db44a872c47483e9771d8ad90b7459b |
|---|
| Source note | uspto-grants-2000_06 |
|---|