6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol → 6-((tetrahydro-2H-pyran-2-yl)oxy)tetrahydrofuro[3,2-b]furan-3(2H)-one

HRID 1053917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053917
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]2[O:13][CH2:14][CH:15]([OH:16])[CH:11]2[O:10][CH2:9]1>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH:12]2[O:13][CH2:14][C:15](=[O:16])[CH:11]2[O:10][CH2:9]1

Komponenten

3

Edukt 1

HCID 767032036-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

Produkt 1

HCID 1183879426-((tetrahydro-2H-pyran-2-yl)oxy)tetrahydrofuro[3,2-b]furan-3(2H)-oneAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

To a solution of 6-((tetrahydro-2H-pyran-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (5.0 g, 21.7 mmol) in DCM (150 mL) was added DMP (18.4 g, 43.5 mmol) at rt, and then the mixture was stirred at 30° C. overnight and concentrated in vacuo. The residue was dissolved in water (150 mL), and extracted with EtOAc (150 mL×3). The combined organic phases were washed with brine (300 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1) to give the title compound as yellow oil (4.96 g, 98%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (150 mL)
  3. extractionextracted with EtOAc (150 mL×3)
  4. washThe combined organic phases were washed with brine (300 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-01fd0b8db1cd4816bb13ab0c8b6fca4d
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394281B2

Notizen zur Reaktion

Wird geladen…