Allyl bromide → HCID 67266810, compound

HRID 1698291Notes

Reaction equation

HRID 1698291 reaction equation
C(=O)([O-])O.[Na+].[CH2:6]([O:11][C:12]1[C@@H:17]([C@H:18]([CH2:20][OH:21])[OH:19])[O:16][C:14](=[O:15])[C:13]=1[OH:22])[CH:7]([CH2:9][OH:10])[OH:8].[CH2:23](Br)[CH:24]=[CH2:25]>O>[CH2:6]([O:11][C:12]1[C@@H:17]([C@H:18]([CH2:20][OH:21])[OH:19])[O:16][C:14](=[O:15])[C:13]=1[O:22][CH2:25][CH:24]=[CH2:23])[CH:7]([CH2:9][OH:10])[OH:8]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 672677953-Glyceryl ascorbate

Product 1

HCID 67266810HCID 67266810, compoundYield 152.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an argon atmosphere, water and sodium hydrogen carbonate (1.42 g) were added to 3-O-glyceryl ascorbic acid (1.42 g) obtained in Example 1, and the mixture was stirred at room temperature for 30 minutes. To the mixture, allyl bromide (2.45 g) was added, and the resultant mixture was heated up to 60° C. and stirred for 2 hours. Thereafter, the mixture was concentrated under reduced pressure, then, dissolved in methanol. Then, the resultant solution was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and 6.70 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:10/3/0.4), and concentration was performed under reduced pressure to obtain to obtain 3-O-glyceryl-2-O-allyl ascorbic acid (2.51 g).

Workup

  1. stirringstirred for 2 hours
  2. concentrationThereafter, the mixture was concentrated under reduced pressure
  3. dissolutiondissolved in methanol
  4. dry with materialThen, the resultant solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure, and 6.70 g of the resultant residue
  6. washElution
  7. concentrationwas performed with chloroform/methanol/water(volume ratio:10/3/0.4), and concentration
  8. customto obtain

Sources & evidence

ORD record
ord-90570c7389324e139b19d5fbb0187655
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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