Benzyl Bromide → HCID 86714024, compound

HRID 1410298Notes

Reaction equation

HRID 1410298 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C@H:22]1[C@H:27]([OH:28])[C@@H:26]([OH:29])[C@H:25]([OH:30])[C@@H:24]([CH2:31][OH:32])[O:23]1)[CH:2]=[CH2:3].[H-].[Na+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C=O>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C@H:22]1[C@H:27]([O:28][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:26]([O:29][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:25]([O:30][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:24]([CH2:31][O:32][CH2:22][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:5]=2)[O:23]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86714025HCID 86714025, compound

Product 1

HCID 86714024HCID 86714024, compoundYield 200%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tetraol (13, 8.4 g, 18 mmol) from Step 2 in N,N-dimethylformamide (100 mL) at 0° C. under an atmosphere of nitrogen was added sodium hydride (60% dispersion in mineral oil, 10.1 g, 252 mmol), and the mixture was stirred for 30 min at the same temperature. Then benzyl bromide (19.5 mL, 162 mmol) was added dropwise, and the mixture was stirred with gradual warming to ambient temperature over 5 h. After re-cooling to 0° C., the reaction mixture was quenched by addition of water (100 mL). The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 5 to 20% tetrahydrofuran in hexanes gradient) to yield the title compound (19, 14.8 g, 18 mmol, 100%) as a white solid.

Workup

  1. stirringthe mixture was stirred
  2. temperatureAfter re-cooling to 0° C.
  3. customthe reaction mixture was quenched by addition of water (100 mL)
  4. additionThe mixture was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 5 to 20% tetrahydrofuran in hexanes gradient)

Sources & evidence

ORD record
ord-82c292dc820e4bd7b98ae148faef62c8
Source dataset
uspto-grants-2014_12
Patent number
US08921412B2

Reaction notes

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