Benzyl Bromide → HCID 131729660, compound

HRID 1698293Notes

Reaction equation

HRID 1698293 reaction equation
[CH2:1]([O:3][C:4]1[C@@:9]([CH2:14][CH:15]([CH2:17][OH:18])[OH:16])([C@H:10]([CH2:12][OH:13])[OH:11])[O:8][C:6](=[O:7])[C:5]=1[OH:19])[CH3:2].C(=O)([O-])O.[Na+].[CH2:25](Br)[C:26]1C=CC=[CH:28][CH:27]=1>CS(C)=O>[CH2:1]([O:3][C:4]1[C@@:9]([CH2:14][CH:15]([CH2:17][OH:18])[OH:16])([C@H:10]([CH2:12][OH:13])[OH:11])[O:8][C:6](=[O:7])[C:5]=1[O:19][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 131729661HCID 131729661, compound

Product 1

HCID 131729660HCID 131729660, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, 3-O-ethylglyceryl ascorbic acid (3.03 g) obtained in Example 7 was stirred in DMSO (10 mL), and further, sodium hydrogen carbonate (0.92 g) and benzyl bromide (1.79 g) were added. The mixture was heated up to 100° 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 2.16 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:20/3/0.3), and concentration was performed under reduced pressure to obtain 3-O-ethylglyceryl-2-O-butyl ascorbic acid (0.89 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThen, the extracted liquid was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure, and 2.16 g of the resultant residue
  4. washElution
  5. concentrationwas performed with chloroform/methanol/water(volume ratio:20/3/0.3), and concentration

Sources & evidence

ORD record
ord-274cb40bd3e647c4bad0a825d6c16788
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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