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2-Methoxypropene → HCID 69280805, Verbindung

HRID 1396301
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1396301
[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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Komponenten

5

Edukt 3

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

Produkt 1

HCID 69280805HCID 69280805, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a89aa5623efe4ae49ae5a2b5fa8ecd76
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08901087B2

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