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

HRID 1676007Notes

Reaction equation

HRID 1676007 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c82ede661d8f40c99a06aa15a981fdb5
Source dataset
uspto-grants-2011_08
Patent number
US08003811B2

Reaction notes

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