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Methanol → (3S,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol

HRID 1643410
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1643410
C([O:9][C@H:10]1[CH2:14][O:13][C@@H:12]2[C@@H:15]([O:18]C(=O)C3C=CC=CC=3)[CH2:16][O:17][C@H:11]12)(=O)C1C=CC=CC=1.[OH-].[Na+].CO>O1CCCC1>[O:13]1[CH2:14][C@H:10]([OH:9])[C@H:11]2[O:17][CH2:16][C@H:15]([OH:18])[C@@H:12]12
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Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11199023(3S,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl dibenzoate

Produkt 1

HCID 12304539(3S,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To (3S,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diyl dibenzoate (6.30 g, 17.8 mmol), a mix of NaOH 10%:MeOH=1:1 (60 mL) was added. After stirring at room temperature for 24 hrs, the solvent was evaporated under reduced pressure. Water (30 mL) was added and extraction with EtOAc (30 mL) was carried out. The aqueous layer (pH adjusted to 6 with H3PO4 5%) was evaporated under reduced pressure to leave a white residue. Tetrahydrofuran was added in a large amount, then the suspension was filtered and the filtrate was concentrated to give the title product as a white solid.

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater (30 mL) was added
  3. extractionextraction with EtOAc (30 mL)
  4. customwas evaporated under reduced pressure
  5. customto leave a white residue
  6. filtrationthe suspension was filtered
  7. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-f8cc545084ca4247aa9137f50e8c391e
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08119806B2

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