참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | proline dl-form | HCID 614 | — |
| 반응물 | Allyl Alcohol | HCID 7858 | — |
| 반응물 | Tetrahydro-4H-pyran-4-one | HCID 121599 | — |
| 반응물 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 촉매 | Palladium, di-mu-chlorobis(eta3-2-propenyl)di- | HCID 61538 | — |
| 용매 | Dimethyl Sulfoxide | HCID 679 | — |
| 생성물 | 3-allyltetrahydro-4H-pyran-4-one | HCID 21077908 | — |
반응 단계
A mixture of tetrahydro-4H-pyran-4-one (6-1) (5.17 g, 51.7 mmol), prop-2-en-1-ol (1.00 g, 17.2 mmol), allylPalladium Chloride dimer (0.157 g, 0.430 mmol), Xantphos (0.498 g, 0.861 mmol), and DL-proline (0.595 g, 5.17 mmol) in DMSO (35 mL) was degassed (2×pump/N2) and heated to 70° C. overnight. The mixture was cooled to rt and partitioned between water and Et2O. Extracted with Et2O. The combined organics were washed with 1:1 brine:water, dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 5.70-5.80 (m, 1H), 5.01-5.09 (m, 2H), 4.13-4.22 (m, 2H), 3.72-3.79 (m, 1H), 3.43 (t, 1H, J=11.2 Hz), 2.52-2.66 (m, 3H), 2.39-2.47 (m, 1H), 1.99-2.07 (m, 1H).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08829196B2 |
|---|
| 출처 데이터셋 | uspto-grants-2014_09 |
|---|
| ORD ID | ord-a0097975223e4495a57662e38607861e |
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| 출처 메모 | uspto-grants-2014_09 |
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