Methyl iodide → 3-(Benzyloxy)-6-methoxyhexahydrofuro[3,2-b]furan

HRID 1053930Notes

Reaction equation

HRID 1053930 reaction equation
[CH2:1]([O:8][CH:9]1[CH:13]2[O:14][CH2:15][CH:16]([OH:17])[CH:12]2[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Na].I[CH3:21]>C(#N)C>[CH2:1]([O:8][CH:9]1[CH2:10][O:11][CH:12]2[CH:16]([O:17][CH3:21])[CH2:15][O:14][CH:13]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 212745236-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-olHCID 178526212HCID 178526212, compound

Product 1

HCID 1183879853-(Benzyloxy)-6-methoxyhexahydrofuro[3,2-b]furanYield 92.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 6-(benzyloxy)hexahydrofuro[3,2-b]furan-3-ol (8.1 g, 34 mmol) in acetonitrile (100 mL) was added hydroxyl sodium (4.12 g, 103 mmol) and iodomethane (9.76 g, 68.8 mmol). The reaction was heated to 45° C. for 8 h and concentrated in vacuo. The residue was diluted with EtOAc (500 mL) and filtered. The filtrate was washed with H2O (50 mL×3), dried with Na2SO4 filtered and concentrated in vacuo to give the title compound as yellow oil (7.84 g, 91.4%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with EtOAc (500 mL)
  3. filtrationfiltered
  4. washThe filtrate was washed with H2O (50 mL×3)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c1c722e022049aa82dd2b74eeb36d91
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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