Benzyl Bromide → 6-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-ol
Reaction equation
[H-].[Na+].[CH2:3]1[O:7][C@@H:6]2[C@@H:8]([OH:11])[CH2:9][O:10][C@@H:5]2[C@@H:4]1[OH:12].[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1>CN(C=O)C>[CH2:19]([O:12][CH:4]1[CH:5]2[O:10][CH2:9][CH:8]([OH:11])[CH:6]2[O:7][CH2:3]1)[C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of NaH (60% mineral oil suspension, 3.28 g, 82.1 mmol) in DMF (135 mL) at 0° C. was added a solution of isobide (10.00 g, 68.4 mmol) in DMF (10 mL) dropwise. After addition, the reaction mixture was stirred at 0° C. for 30 min, then BnBr (14.04 g, 82.1 mmol) was added too. The resulting mixture was allowed to stir at rt overnight and concentrated in vacuo. The residue was dissolved in water (100 mL), and extracted with EtOAc (200 mL×3). The combined organic phases were washed with brine (200 mL×3), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/10) to give the title compound as yellow oil (10.36 g, 64.1%).
Workup
- additionAfter addition
- stirringto stir at rt overnight
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in water (100 mL)
- extractionextracted with EtOAc (200 mL×3)
- washThe combined organic phases were washed with brine (200 mL×3)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/10)
Sources & evidence
- ORD record
- ord-b7bcb8fefd96421391e248be116b885b
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394281B2
Reaction notes
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