HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 57438392, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 3-Iodobenzyl alcohol | HCID 42300 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | 1-(3-Chloro-2,4-dihydroxy-phenyl)ethanone | HCID 57438294 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57438392 | HCID 57438392 | 64.5% |
Reaction Steps
Add triphenylphosphine (13.6 g, 51.7 mmol) and DIAD (10.5 g, 51.7 mmol) to a solution of (3-iodo-phenyl)-methanol (11.0 g, 47.0 mmol) and 1-(3-Chloro-2,4-dihydroxy-phenyl)-ethanone (8.77 g, 47.0 mmol) in dichloromethane:tetrahydrofuran (250 ml:250 ml) and stir. After 18 hours, concentrate the reaction, and load directly onto silica. Purify the residue by flash chromatography eluting with acetone:hexanes to yield the title product as a white solid (12.2 g, 64%): 1H NMR (DMSO-d6) δ 2.62 (s, 3H), 5.34 (s, 2H), 6.88 (d, 1H), 7.23 (t, 1H), 7.48 (d, 1H), 7.72 (d, 1H), 7.87 (s, 1H), 7.96 (d, 1H), 13.14 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07816523B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-f0a3dc7b3e7a4ff980f6d097a831eb92 |
| Source note | uspto-grants-2010_10 |