Diethyl Ether → HCID 19737925, compound

HRID 1494278Notes

Reaction equation

HRID 1494278 reaction equation
[Mn]([O-])(=O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[CH:23]([C:25]1[C:33]2[C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[O:30][C:29]=2[CH:28]=[C:27]([Sn:38]([CH3:41])([CH3:40])[CH3:39])[CH:26]=1)=[O:24].S([O-])([O-])(=O)=[O:43].[Na+].[Na+].CCOCC>N1C=CC=CC=1>[C:23]([C:25]1[C:33]2[C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[O:30][C:29]=2[CH:28]=[C:27]([Sn:38]([CH3:41])([CH3:40])[CH3:39])[CH:26]=1)([OH:43])=[O:24]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24436Sodium SulfateHCID 11760202Tetrabutylammonium permanganateHCID 19737920HCID 19737920, compound

Product 1

HCID 19737925HCID 19737925, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of tetra-n-butylammonium permanganate (5.1 g, 14.0 mmol) in anhydrous pyridine (35 mL) was transferred via cannula needle into a solution of the stannane 305 (5.0 g, 14.0 mmol) in anhydrous pyridine (35 mL) at 0° C. under a nitrogen atmosphere. The reaction was stirred for 30 min., then saturated aqueous sodium sulfate (50 mL) was added to quench the reaction. The mixture was then poured into ether and the layers separated. The organic layer was washed with 2N aqueous HCl (6 times with 100 mL), water (2 times) and then brine (2 times). The solution was dried with magnesium sulfate, then filtered and concentrated under vacuum to provide 4.8 g (92% yield) of the stannane 306 as a white solid.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe layers separated
  4. washThe organic layer was washed with 2N aqueous HCl (6 times with 100 mL), water (2 times)
  5. dry with materialThe solution was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ded39416ac484c6fabf93477d09d710c
Source dataset
uspto-grants-1991_06
Patent number
US05025008

Reaction notes

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