Hydrogen Bromide → HCID 54105575, compound

HRID 728486Notes

Reaction equation

HRID 728486 reaction equation
BrN1C(=[O:7])CCC1=O.Br.[C:10]([O:18][CH:19]([CH3:33])[CH2:20][CH:21]1[CH2:26][O:25][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:23][CH2:22]1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[C:24]([O:25][CH2:26][CH:21]([CH2:20][CH:19]([O:18][C:10](=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:33])[CH2:22][OH:7])(=[O:23])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 19884220HCID 19884220, compound

Product 1

HCID 54105575HCID 54105575, compoundYield 29.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred and ice cooled suspension of 9.344 g (52.5 mM) of N-bromosuccinimide in 250 ml of water are added a drop of conc. hydrobromic acid and 17.125 g of the crude 5-(2-benzoyloxypropan-1-yl)-2-phenyl-1,3-dioxane m4 obtained in the previous reaction dropwise. After standing at 0° C. for another 1 hour, 22 g (260 mM) of sodium bicarbonate is added to the reaction mixture and the product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. Purification of the product by column silica gel chromatography using n-hexane-ethyl acetate (1:1) as an eluent gives 7.401 g (29.7% yield from the compound m2) of the titled compound m5 as an oily product.

Workup

  1. temperatureice cooled
  2. customobtained in the previous reaction dropwise
  3. washThe ethyl acetate layer is washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customPurification of the product by column silica gel chromatography

Sources & evidence

ORD record
ord-82dae75b62d444e7b6b652179fe0d91f
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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