Sodium hydride → 6-(2-(Benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 1053923Notes

Reaction equation

HRID 1053923 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.[H-].[Na+].Br[CH2:14][CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([O:16][CH2:15][CH2:14][O:6][CH:4]1[CH:3]2[O:7][CH2:8][CH:9]([OH:10])[CH:2]2[O:1][CH2:5]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 999371,4:3,6-Dianhydromannitol

Product 1

HCID 1183879956-(2-(Benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan-3-olYield 27.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of hexahydrofuro[3,2-b]furan-3,6-diol (7.50 g, 51.37 mmol) in anhydrous DMF (100 mL) was added sodium hydride (60% mineral oil suspension, 2.90 g, 72.39 mmol) at 0° C. in portions under the nitrogen atmosphere. Then the mixture was moved to room temperature and stirred for 15 min. To the mixture was added 2-bromoethoxymethylbenzene (12.26 g, 56.97 mmol), and then the mixture was stirred at 115° C. overnight. The mixture was quenched with water (100 mL), and extracted with DCM (300 mL×3). The combined organic phases were washed with brine (200 mLx3), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica chromatography (EtOAc/PE (v/v)=1/2) to give the title compound as brown liquid (3.90 g, 27%).

Workup

  1. customwas moved to room temperature
  2. stirringthe mixture was stirred at 115° C. overnight
  3. customThe mixture was quenched with water (100 mL)
  4. extractionextracted with DCM (300 mL×3)
  5. washThe combined organic phases were washed with brine (200 mLx3)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica chromatography (EtOAc/PE (v/v)=1/2)

Sources & evidence

ORD record
ord-41b94d2f4f784e48a6e8a23f5e478bce
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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