Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Butyn-2-ol | HCID 16239 | — |
| Reactant | Benzoic acid, 2-iodo-, methyl ester | HCID 69132 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 11816547 | HCID 11816547 | — |
Reaction Steps
Pd(PPh3)4 (1.9 g, 0.006 eq) and CuI (2.6 g, 0.05 eq) were suspended in DMF (350 ml). Methyl 2-iodobenzoate (70.8 g, 1 eq), but-3-yn-2-ol (32 ml, 1.5 eq), TEA (75 ml, 2 eq) were added under nitrogen atmosphere and the mixture was stirred at 60° C. for 6 hrs and at RT. overnight. The precipitated solid was filtered off, the mother liquors was diluted with a saturated solution of NaClaqueous and extracted with EtOAc (twice). The collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound, as a brownish thick oil (47.7 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09321776B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-da96d5edd40b4e7b93853eb445c2ef31 |
|---|
| Source note | uspto-grants-2016_04 |
|---|
