Benzyl Bromide → HCID 86641125, compound

HRID 2191043Notes

Reaction equation

HRID 2191043 reaction equation
[CH3:1][O:2][C@@H:3]1[C@@H:8]2[C@H:6]([O:7]2)[C@@H:5]([CH2:9][OH:10])[O:4]1.[H-].[Na+].[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1>O1CCOCC1>[CH2:19]([O:10][CH2:9][C@H:5]1[O:4][C@H:3]([O:2][CH3:1])[C@@H:8]2[C@@H:6]1[O:7]2)[C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86641124HCID 86641124, compound

Product 1

HCID 86641125HCID 86641125, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 35.6 (20 g, 137 mmol) was dissolved in 15 mL dioxane, cooled to 0° C. and treated with 60% NaH (6.0 g, 151 mmol). The mixture was stirred at 0° C. for 30 min and then treated with BnBr (18 mL, 151 mmol). The mixture was warmed to r.t., stirred for 3 h, and then quenched with 50 mL MeOH. The mixture was stirred for another 30 min and the solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 10-50% EtOAc in Hexane to give compound 35.7 (26.55 g, 82% yield).

Workup

  1. temperatureThe mixture was warmed to r.t.
  2. stirringstirred for 3 h
  3. customquenched with 50 mL MeOH
  4. stirringThe mixture was stirred for another 30 min
  5. customthe solvent was evaporated under reduced pressure
  6. washeluting with 10-50% EtOAc in Hexane

Sources & evidence

ORD record
ord-247351ea918c45f7b30edf33cee9f9d2
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

Loading…