Glycidol → HCID 131729667, compound

HRID 1698297Notes

Reaction equation

HRID 1698297 reaction equation
[CH2:1]([O:5][C:6]1[C@@:11]([CH2:16][CH:17]([CH2:19][OH:20])[OH:18])([C@H:12]([CH2:14][OH:15])[OH:13])[O:10][C:8](=[O:9])[C:7]=1[OH:21])[CH2:2][CH2:3][CH3:4].C(=O)([O-])O.[Na+].[CH2:27]1[O:29][CH:28]1[CH2:30][OH:31]>CS(C)=O>[CH2:1]([O:5][C:6]1[C@@:11]([CH2:16][CH:17]([CH2:19][OH:20])[OH:18])([C@H:12]([CH2:14][OH:15])[OH:13])[O:10][C:8](=[O:9])[C:7]=1[O:21][CH2:27][CH:28]([CH2:30][OH:31])[OH:29])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11164GlycidolHCID 516892Sodium BicarbonateHCID 131729663HCID 131729663, compound

Product 1

HCID 131729667HCID 131729667, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, 3-O-butylglyceryl ascorbic acid (4.98 g) obtained in Example 6 was stirred in DMSO(10 mL), and further, sodium hydrogen carbonate (0.33 g) was added. Thereafter, glycidol (1.46 g) was added and the mixture was heated up to 80° C. and stirred for 18 hours, followed by extraction with n-butnol. The extracted liquid was dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and 6.23 g of the resultant residue was subjected to silica gel column chromatography. Elution was performed with chloroform/methanol/water(volume ratio:20/3/0.4), and concentration was performed under reduced pressure to obtain 3-O-butylglyceryl-2-O-glyceryl ascorbic acid (1.23 g).

Workup

  1. extractionfollowed by extraction with n-butnol
  2. dry with materialThe extracted liquid was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure, and 6.23 g of the resultant residue
  4. washElution
  5. concentrationwas performed with chloroform/methanol/water(volume ratio:20/3/0.4), and concentration

Sources & evidence

ORD record
ord-974752728079414aae36ea2ec5d4a092
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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