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2-Methoxypropene → HCID 69280805, 화합물

HRID 1396301
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HRID 1396301 반응식
[C:1]([O:9][CH2:10][C@H:11]1[O:19][C@H:18]2[C@H:14]([N:15]=[C:16]([N:20]([CH3:22])[CH3:21])[S:17]2)[C@@H:13]([OH:23])[C@@H:12]1[OH:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH3:26][C:27]1C=CC(S(O)(=O)=O)=C[CH:28]=1.COC(C)=C>CN(C=O)C>[C:1]([O:9][CH2:10][C@@H:11]1[C@@H:12]2[C@H:13]([O:23][C:27]([CH3:28])([CH3:26])[O:24]2)[C@@H:14]2[C@@H:18]([S:17][C:16]([N:20]([CH3:21])[CH3:22])=[N:15]2)[O:19]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 83002-MethoxypropeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 69083776HCID 69083776, 화합물

생성물 1

HCID 69280805HCID 69280805, 화합물수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 154 (3.0 g, 8.5 mmol) in DMF (20 mL) was added 4-methylbenzenesulfonic acid hydrate (3.2 g, 17 mmol) and 2-methoxyprop-1-ene (6.1 g, 85 mmol) sequentially. The resulting solution was stirred for 15 minutes at room temperature, before the reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (20 mL), which was then extracted with dichloromethane (3×20 mL). The combined organic layer was washed with brine (2×10 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The crude residue was purified by flash column chromatography with 1%-10% ethyl acetate in petroleum ether to afford 155 as an off-white solid (1.6 g, 48%). (ES, m/z): [M+H]+ 393.0; 1H NMR (300 MHz, CDCl3) δ 8.08-8.05 (m, 2H), 7.63-7.45 (m, 3H), 6.32-6.30 (m, 1H), 4.60-4.52 (m, 2H), 4.41-4.31 (m, 2H), 3.97-3.91 (m, 1H), 3.70-3.63 (m, 1H), 3.55-3.50 (m, 1H), 3.39-3.30 (m, 1H), 3.10 (s, 6H), 1.50 (s, 6H).

후처리

  1. customwas quenched by the addition of saturated aqueous sodium bicarbonate solution (20 mL), which
  2. extractionwas then extracted with dichloromethane (3×20 mL)
  3. washThe combined organic layer was washed with brine (2×10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude residue was purified by flash column chromatography with 1%-10% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-a89aa5623efe4ae49ae5a2b5fa8ecd76
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901087B2

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