HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diazomethane → 1-(3-{[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-phenyl)-2-chloro-ethanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diazomethane | HCID 9550 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 3-{[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acid | HCID 57884471 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(3-{[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-phenyl)-2-chloro-ethanone | HCID 86620599 | 100% |
Reaction Steps
Add oxalyl chloride (256 mg, 2.02 mmol) to a solution of 3-{[4-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acid (0.786 mg, 1.84 mmol) in tetrahydrofuran (0.20M). Add dimethylformamide (5 drops). Add ethereal solution of diazomethane (1.90 mmol) and stir for 2 hours. Add hydrochloric acid (4N in dioxane) to quench unreacted diazomethane and evaporate solvents to afford the title compound (0.786 mg, 1.84 mmol, 94%): MS (m/z): 457 (M−H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07816523B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-42d03f24d80a41059693be64caab0228 |
| Source note | uspto-grants-2010_10 |