3,4-dihydro-2H-pyran → 6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 1053916Notes

Reaction equation

HRID 1053916 reaction equation
[O:1]1[CH2:5][CH:4]([OH:6])[CH:3]2[O:7][CH2:8][CH:9]([OH:10])[CH:2]12.[CH2:11]1[CH2:16][O:15][CH:14]=[CH:13][CH2:12]1>C(Cl)Cl>[O:15]1[CH2:16][CH2:11][CH2:12][CH2:13][CH:14]1[O:6][CH:4]1[CH:3]2[O:7][CH2:8][CH:9]([OH:10])[CH:2]2[O:1][CH2:5]1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 999371,4:3,6-Dianhydromannitol

Product 1

HCID 767032036-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-olYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of hexahydrofuro[3,2-b]furan-3,6-diol (10.0 g, 68.50 mmol) in DCM (150 mL) was added PPTs (1.7 g, 6.85 mmol) at rt followed by DHP (6.0 g, 71.90 mmol) slowly in 2 h, and then the mixture was stirred at rt 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), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=1/1) to give the title compound as a white solid (7.1 g, 45%).

Workup

  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)=1/1)

Sources & evidence

ORD record
ord-7d662ef3abdb445ea8536911dd8c7444
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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