Benzyl Bromide → HCID 131720909, compound

HRID 355328Notes

Reaction equation

HRID 355328 reaction equation
[O:1]([CH3:12])[C@@H:2]1[O:10][C@@H:9]([CH3:11])[C@@H:7]([OH:8])[C@@H:5]([OH:6])[C@@H:3]1[OH:4].[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1.[H-].[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].C1COCC1>[O:1]([C:12]([CH2:19][C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)([CH2:19][C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)[CH2:19][C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1)[C@@H:2]1[O:10][C@@H:9]([CH3:11])[C@@H:7]([OH:8])[C@@H:5]([OH:6])[C@@H:3]1[OH:4]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 44657814687-15-1

Product 1

HCID 131720909HCID 131720909, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl α-L-fucopyranoside (1.96 g, 9.61 mmol; Aldrich, Sigma), BnBr (8 mL, 67.3 mmol; benzyl bromide), and TBAI (177 mg, 048 mmol; tetrabutylammonium iodide; Aldrich) in THF (20 mL; tetrahydrofuran) at 0° C. was added NaH (2.35 g, 57.6 mmol). The cooling bath was removed and the reaction mixture was allowed to stir for 24 h. The reaction was diluted with EtOAc (50 mL; ethyl acetate) and poured into a saturated NH4Cl solution (50 mL). The aqueous phase was extracted with EtOAc (2×30 mL) and the combined organic phases were dried (MgSO4) and concentrated under reduced pressure providing the crude oil. Purification by silica gel flash chromatography (hexane:EtOAc, 100% to 9:1 to 1:1) gave the desired product in excellent yield (5.0 g, 92%).

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was diluted with EtOAc (50 mL; ethyl acetate)
  3. additionpoured into a saturated NH4Cl solution (50 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (2×30 mL)
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customproviding the crude oil
  8. customPurification by silica gel flash chromatography (hexane:EtOAc, 100% to 9:1 to 1:1)

Sources & evidence

ORD record
ord-5103a3efac184d8ebe2bd0adba13d3bd
Source dataset
uspto-grants-1998_11
Patent number
US05830871

Reaction notes

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