Benzyl Bromide → HCID 54410149, compound

HRID 650218Notes

Reaction equation

HRID 650218 reaction equation
C([Sn](=O)CCCC)CCC.[O:11]([C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)[C@@H:12]1[O:20][C@H:19]([CH2:21][OH:22])[C@H:17]([OH:18])[C@H:15]([OH:16])[C@H:13]1[OH:14].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(Cl)Cl.CO.N>O1CCOCC1>[CH2:32]([O:16][C@H:15]1[C@@H:17]([OH:18])[C@@H:19]([CH2:21][OH:22])[O:20][C@@H:12]([O:11][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)[C@@H:13]1[OH:14])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 61221Dibutyltin oxideHCID 651154-NitrophenylgalactosideHCID 21584172Ammonia methanol dichloromethane

Product 1

HCID 54410149HCID 54410149, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dibutyltin oxide (1.87 g, 7.5 mmol) is added to a solution of p-nitrophenyl β-D-galactopyranoside (1.5 g, 5.0 mmol) in absolute dioxane (40 ml) and the mixture is heated under reflux. After 3 hours, benzyl bromide (3.6 ml, 30 mmol) are added to the solution obtained and the batch is stirred under reflux for a further 48 hours. The solvent is then distilled off in vacuo and the residue is purified by flash chromatography (ethyl acetate/petroleum ether 2:1→1:1]. Colourless crystals (1.58 g 81%) are obtained; TLC [methylene chloride/methanol/ammonia (25%) 15:3:0.2]: Rf=0.69; melting point=127° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. customobtained
  4. temperatureunder reflux for a further 48 hours
  5. distillationThe solvent is then distilled off in vacuo
  6. customthe residue is purified by flash chromatography (ethyl acetate/petroleum ether 2:1→1:1]
  7. customColourless crystals (1.58 g 81%) are obtained

Sources & evidence

ORD record
ord-826400f6b42845ec96024794699721ca
Source dataset
uspto-grants-2001_08
Patent number
US06271342B1

Reaction notes

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