MeOH tetrahydrofuran → HCID 70556657, compound

HRID 1503815Notes

Reaction equation

HRID 1503815 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([S:14][CH3:15])[CH:13]=1.CO.[O:21]1CCCC1>O.C(OCC)C>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([N+:16]([O-:18])=[O:17])=[C:12]([S:14]([CH3:15])=[O:21])[CH:13]=1

Participants

6

Reactant 3

HCID 21899815MeOH tetrahydrofuranHCID 23667635Sodium periodateHCID 69435785HCID 69435785, compound

Product 1

HCID 70556657HCID 70556657, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium periodate (4.2 g, 16.34 mmol) in water (8 mL) was added to the solution of the product of Example 14A (4.01 g, 16.34 mmol) in 2/1 methanol/tetrahydrofuran (60 mL) and the mixture stirred for 1 hour. The mixture was diluted with ethyl ether, washed with water and saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 3/1 ether/ethyl acetate to provide the title compound.

Workup

  1. washwashed with water and saturated aqueous sodium bicarbonate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  6. washeluting with 3/1 ether/ethyl acetate

Sources & evidence

ORD record
ord-8115b883f17c4525be50367aafeeac7f
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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