3-(Benzyloxy)-6-methoxyhexahydrofuro[3,2-b]furan → 6-Methoxyhexahydrofuro[3,2-b]furan-3-ol

HRID 1053931Notes

Reaction equation

HRID 1053931 reaction equation
C([O:8][CH:9]1[CH2:13][O:12][CH:11]2[CH:14]([O:17][CH3:18])[CH2:15][O:16][CH:10]12)C1C=CC=CC=1>CCO.[Pd]>[CH3:18][O:17][CH:14]1[CH:11]2[O:12][CH2:13][CH:9]([OH:8])[CH:10]2[O:16][CH2:15]1

Participants

4

Reactant 1

HCID 1183879853-(Benzyloxy)-6-methoxyhexahydrofuro[3,2-b]furan

Product 1

HCID 2373216-Methoxyhexahydrofuro[3,2-b]furan-3-olYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(benzyloxy)-6-methoxyhexahydrofuro[3,2-b]furan (7.84 g, 31.3 mmol) in EtOH (80 mL) was added Pd/C (10%, 812 mg). The reaction was stirred at rt for two days under H2 atmosphere and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=1/1) to give the title compound as colorless oil (4.53 g, 90.3%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=1/1)

Sources & evidence

ORD record
ord-da121d82ac914ad5ac7ec695e95c9d7d
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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