Allyl bromide → HCID 131729666, compound

HRID 1698296Notes

Reaction equation

HRID 1698296 reaction equation
C(=O)([O-])O.[Na+].[CH2:6]([O:10][C:11]1[C@@:16]([CH2:21][CH:22]([CH2:24][OH:25])[OH:23])([C@H:17]([CH2:19][OH:20])[OH:18])[O:15][C:13](=[O:14])[C:12]=1[OH:26])[CH2:7][CH2:8][CH3:9].[CH2:27](Br)[CH:28]=[CH2:29]>O>[CH2:6]([O:10][C:11]1[C@@:16]([CH2:21][CH:22]([CH2:24][OH:25])[OH:23])([C@H:17]([CH2:19][OH:20])[OH:18])[O:15][C:13](=[O:14])[C:12]=1[O:26][CH2:29][CH:28]=[CH2:27])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 131729663HCID 131729663, compound

Product 1

HCID 131729666HCID 131729666, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an argon atmosphere, water and sodium hydrogen carbonate (0.98 g) were added to 3-O-butylglyceryl ascorbic acid (3.56 g) obtained in Example 6, and the mixture was stirred at room temperature for 30 minutes. To the mixture, allyl bromide (1.68 g) was added, and the resultant mixture was heated up to 60° C. and stirred for 5 hours, followed by extraction with ethyl acetate. Then, the extracted liquid was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and 3.53 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:30/3/0.3), and concentration was performed under reduced pressure to obtain to obtain 3-O-butylglyceryl-2-O-allyl ascorbic acid (3.00 g).

Workup

  1. stirringstirred for 5 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThen, the extracted liquid was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure, and 3.53 g of the resultant residue
  5. washElution
  6. concentrationwas performed with chloroform/methanol/water(volume ratio:30/3/0.3), and concentration
  7. customto obtain

Sources & evidence

ORD record
ord-e090347ee73742eea8f27c5b536df956
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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