Methyl morpholine oxide → HCID 86637429, compound

HRID 2265796Notes

Reaction equation

HRID 2265796 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[OH:9])=[CH:4][C:3]=1[CH2:32]Br.C[N+]1([O-])CC[O:38]CC1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[OH:9])=[CH:4][C:3]=1[CH:32]=[O:38]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxide2×HCID 68421570HCID 68421570, compound

Product 1

HCID 86637429HCID 86637429, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-chloro-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-2-bromomethyl-benzene (2.0 g) in acetonitrile (20 mL) is added N-methylmorpholine-N-oxide (0.47 g). The resulting solution is stirred at ambient temperature for 2 h before more N-methylmorpholine-N-oxide (0.20 g) is added. After stirring at ambient temperature overnight, the solvent is removed under reduced pressure and the residue is filtered over silica gel eluting with dichloromethane.

Workup

  1. additionis added
  2. customthe solvent is removed under reduced pressure
  3. filtrationthe residue is filtered over silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-aa0baf362ba442ce9c8918f6bf5804c5
Source dataset
uspto-grants-2010_12
Patent number
US07858587B2

Reaction notes

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