Potassium Bromide → HCID 12895803, compound

HRID 990911Notes

Reaction equation

HRID 990911 reaction equation
[O:1]=[C:2]1[CH2:9][C@H:8]2[C@H:4]([CH2:5][C@@H:6]([O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[C@H:7]2[CH2:10][OH:11])[O:3]1.C([O-])(=O)C.[Na+].[Br-].[K+].[Cl-].[Na+].O.ClO.[Na].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[O:1]=[C:2]1[CH2:9][C@H:8]2[C@H:4]([CH2:5][C@@H:6]([O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[C@H:7]2[CH:10]=[O:11])[O:3]1

Participants

9

Reactant 6

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 22842863HCID 22842863, compoundHCID 450517377681-52-9HCID 57417360Sodium chloride; water

Product 1

HCID 12895803HCID 12895803, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S,5R,6R,7R)-3-oxo-6-hydroxymethyl-7-(2-tetrahydropyranyloxy)-2-oxabicyclo[3.3.0]octane (140.5 g; J. Am. Chem. Soc., 98, 1490 (1971)) in ethyl acetate (4100 ml), water (410 ml), sodium acetate (134.9 g), potassium bromide (6.53 g) and 2,2,6,6-tetramethyl-1-piperidinyloxyradical (TEMPO; 2.14 g) were added. The mixture was cooled with sodium chloride-water. The reaction mixture was stirred vigorously. Thereto, a solution of 10% sodium hypochlorous acid (302 ml) which was saturated with sodium hydrogencarbonate was added at a dropwise for 40 minutes. After reaction, the organic layer was washed by an aqueous saturated solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the title compound (113.6 g).

Workup

  1. additionwas added at a dropwise for 40 minutes
  2. customAfter reaction
  3. washthe organic layer was washed by an aqueous saturated solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbf367521bd243a1af3f216e4bc7ecf5
Source dataset
uspto-grants-2002_10
Patent number
US06462081B1

Reaction notes

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