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3,4-dihydro-2H-pyran → HCID 117874872, Verbindung

HRID 517369
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 517369
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[O:6][CH2:7][C@H:8]([OH:21])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:18]2[C@@H:14]([O:15][C:16](=[O:19])[CH2:17]2)[CH2:13][C@H:12]1[OH:20].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.[C:33](=[O:36])(O)[O-].[Na+]>C1COCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]1[O:20][C@@H:12]1[CH2:13][C@@H:14]2[O:15][C:16](=[O:19])[CH2:17][C@@H:18]2[C@H:11]1/[CH:10]=[CH:9]/[C@@H:8]([O:21][CH:23]1[CH2:24][CH2:3][CH2:2][CH2:33][O:36]1)[CH2:7][O:6][C:5]1[CH:22]=[CH:23][CH:24]=[C:3]([C:2]([F:25])([F:1])[F:26])[CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 12042328(+)-(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one

Produkt 1

HCID 117874872HCID 117874872, VerbindungAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998
p-Toluenesulfonic acid monohydrate
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

p-Toluenesulfonic acid monohydrate (0.35 g, 1.8 mmol) was added to a solution of (3aR,4R,5R,6aS)-4-((R,E)-4-(3-(trifluoromethyl)phenoxy)-3-hydroxybut-1-enyl)-hexahydro-5-hydroxycyclopenta[b]furan-2-one (15.0 g, 40.3 mmol) and 3,4-dihydro-2H-pyran (8.47 g, 100.7 mmol) in THF (200 mL) at room temperature and the mixture was stirred for 2.5 hr (TLC monitoring). Saturated aqueous solution of sodium bicarbonate (200 mL) was poured into the reaction mixture and the mixture was stirred for 5 minutes. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 mL). The combined organic layers were dried over magnesium sulfate, filtered off solid and concentrated under reduced pressure to give 24.0 g of crude product. The crude product was purified by column chromatography and then concentrated under reduced pressure to provide 19.0 g of the titled compound (87.5% yield).

Aufarbeitung

  1. stirringthe mixture was stirred for 5 minutes
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (200 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered off solid
  6. concentrationconcentrated under reduced pressure
  7. customto give 24.0 g of crude product
  8. customThe crude product was purified by column chromatography
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1c7c69a790fd4f928c2b87e59a89d547
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115109B2

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