Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
3-Ethynylbenzoic acid methyl ester → Methyl 3-((4-(2-acetamidopropyl)phenyl)ethynyl)benzoate
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | 3-Ethynylbenzoic acid methyl ester | HCID 11275159 | — |
| 반응물 | N-(1-(4-Iodophenyl)propan-2-YL)acetamide | HCID 66611344 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 촉매 | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | Methyl 3-((4-(2-acetamidopropyl)phenyl)ethynyl)benzoate | HCID 66611163 | — |
반응 단계
To 10.0 g (63.4 mmol) methyl 3-ethynylbenzoate (J. Org. Chem. 1981, 46, 2280-6) and 7.00 g (23.1 mmol) N-(1-(4-iodo-phenyl)propan-2-yl)acetamide (I52.1) in 80 mL DMF are added 100 mL TEA, 250 mg (1.31 mmol) CuI and 1.20 g (1.71 mmol) bis(triphenylphosphine)-palladium (II) chloride. After stirring over night r.t. the solvents are removed under reduced pressure. The residue is partitioned between EtOAc and diluted aq. NH4Cl solution. The organic layer is separated and the aq. layer is extracted with EtOAc (2×). The org. layers are combined, washed with brine, dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, EtOAc 100%).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US08835472B2 |
| 출처 데이터셋 | uspto-grants-2014_09 |
| ORD ID | ord-80a171854e3a4cd182eb4751a6186526 |
| 출처 메모 | uspto-grants-2014_09 |