참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Dichloromethane | HCID 6344 | — |
| 반응물 | Sodium Bicarbonate | HCID 516892 | — |
| 반응물 | 2-(Furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 2773996 | — |
| 반응물 | 6-Bromo-1-tetralone | HCID 10105069 | — |
| 촉매 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 용매 | Ethyl Acetate | HCID 8857 | — |
| 용매 | 1,4-Dioxane | HCID 31275 | — |
| 생성물 | 7-(furan-3-yl)-3,4-dihydro-2H-1-benzopyran-4-one | HCID 118597919 | 83% |
반응 단계
To a solution of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (1.5 g, 6.6 mmol) in dioxane (6 mL) was added 2-(furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.92 g, 9.9 mmol), Pd(dppf)Cl2.DCM (540 mg, 0.66 mmol) and sat. NaHCO3 (2 mL). The mixture was stirred at 100° C. for 4 h under nitrogen. The mixture was cooled to rt and diluted with EtOAc, filtered, and concentrated. The residue was purified by silica gel chromatography (4:1 PE:EtOAc) to give 1.18 g (83%) of the title compound as white solid. 1H NMR (400 MHz, CDCl3): δ 2.82 (2H, t, J=6.2 Hz), 4.56 (2H, t, J=6.4 Hz), 6.71 (1H, s), 7.07 (1H, s), 7.14 (1H, d, J=8.4 Hz), 7.50 (1H, s), 7.81 (1H, s), 7.88 (1H, d, J=8.4 Hz). [M+H] Calc'd for C13H10O3, 215. Found, 215.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US09447046B2 |
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| 출처 데이터셋 | uspto-grants-2016_09 |
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| ORD ID | ord-75d1b073b3e7499f9287b84fd8750187 |
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| 출처 메모 | uspto-grants-2016_09 |
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