Benzyl Bromide → HCID 15115713, compound

HRID 1199119Notes

Reaction equation

HRID 1199119 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:16][CH:13]([O:14][CH3:15])[CH2:12][C@@H:11]1[OH:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.C1(C)C=CC=CC=1.O.C(=O)([O-])[O-].[Ag+2]>[CH2:18]([O:17][C@@H:11]1[C@@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[O:16][CH:13]([O:14][CH3:15])[CH2:12]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 2

HCID 7498Benzyl BromideHCID 14350981HCID 14350981, compound

Product 1

HCID 15115713HCID 15115713, compound

Reagents, catalysts & solvents 4

HCID 178418647HCID 178418647, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 9.0 g. (0.034 mole) of methyl 5-O-(t-butyldimethylsilyl)-2-deoxyribofuranoside, 15 g (0.19 mole) of benzyl bromide, and 21 g (0.076 mole) silver carbonate in 50 ml dry dimethylformamide or other aprotic solvent is heated at 60° C. under a dry nitrogen atmosphere for five days. The mixture is cooled and the solids filtered. The filtrate is then concentrated at reduced pressure to 30 ml volume. To this are added 20 ml pyridine and the mixture heated at 65° C. for three hours. The solvents are again removed under reduced pressure affording a dark gummy residue which is taken up in a mixture of 150 ml toluene and 100 ml DI water. The organic phase is separated, washed with water (2×100 ml), dried (Na2SO4) and filtered. The solvent is removed at reduced pressure affording the methyl 3-O-benzyl-5-O-(t-butyldimethylsilyl)-2-deoxyribofuranoside compound as a red oil.

Workup

  1. additionA mixture of 9.0 g
  2. temperatureThe mixture is cooled
  3. filtrationthe solids filtered
  4. concentrationThe filtrate is then concentrated at reduced pressure to 30 ml volume
  5. additionTo this are added 20 ml pyridine
  6. customThe solvents are again removed under reduced pressure
  7. customaffording a dark gummy residue which
  8. customThe organic phase is separated
  9. washwashed with water (2×100 ml)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customThe solvent is removed at reduced pressure

Sources & evidence

ORD record
ord-efc675baa5fe4221bc5287fe32827c3a
Source dataset
uspto-grants-1990_02
Patent number
US04898936

Reaction notes

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