4-Nitrobenzyl bromide → HCID 70247805, compound

HRID 428311Notes

Reaction equation

HRID 428311 reaction equation
[N+](C1C=CC(CBr)=CC=1)([O-])=O.[CH2:12]([O:19][CH2:20][C@H:21]([C@H:33]([C@@H:35]([C@@H:37]([CH2:49][O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[O:38]CC1C=CC([N+]([O-])=O)=CC=1)[OH:36])[OH:34])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Ag]=O>[CH2:12]([O:19][CH2:20][C@H:21]([C@H:33]([C@@H:35]([C@@H:37]([CH2:49][O:50][CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[OH:38])[OH:36])[OH:34])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 54111386HCID 54111386, compound

Product 1

HCID 70247805HCID 70247805, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst2×

Procedure

To a solution of 1,6-di-O-benzyl-3,4-O-isopropylidene-D-mannitol, obtained as in example 2, (402 mg, 1 mmol) in toluene (10 mL) was added freshly prepared silver oxide (464 mg, 2 mmol) and 4-nitrobenzylbromide (648 mg, 3 mmol). The suspension was stirred at room temperature overnight. More silver oxide (464 mg, 2 mmol) was added and the reaction was refluxed for 24 h. The insoluble material was filtered off and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 50% EtOAc in hexane to yield 60% of 1,6-di-O-benzyl-2-O-(4-nitrobenzyl)-D-mannitol and 12% of 1,6-di-O-benzyl-2,5-di-O-(4-nitrobenzyl)-D-mannitol.

Workup

  1. temperaturethe reaction was refluxed for 24 h
  2. filtrationThe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel eluting with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-3d1c6d7e7ef74a388dbfb87fb419fc96
Source dataset
uspto-grants-2001_11
Patent number
US06313177B1

Reaction notes

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