Dimethyl Sulfoxide → HCID 18600208, compound

HRID 1583569Notes

Reaction equation

HRID 1583569 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].C[O-].[Na+].[CH2:16](I)[CH2:17][CH2:18][CH3:19].CS(C)=O>C(OCC)(=O)C>[CH2:16]([O:6][C:5]1[C@@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[O:8][C:2](=[O:1])[C:3]=1[OH:4])[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10962Butyl iodideHCID 10942334Sodium MethoxideHCID 54670067L-Ascorbic Acid

Product 1

HCID 18600208HCID 18600208, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture was prepared containing the following ingredients: 33 g. of L-ascorbic acid, 10.2 g. of sodium methylate, 34.5 g. of n-butyl iodide and 250 ml. of DMSO. The reaction mixture was stirred at ambient temperature and the progress of the reaction monitored by thin layer chromatography. After 24 hours, the reaction mixture was added to 500 ml. of ethyl acetate. 3-O-n-Butyl-L-ascorbic acid formed in the above reaction precipitated and was separated by filtration. Further precipitation was caused by adding 300 ml. of toluene to the filtrate. These crystals were also collected and the combined crystals dissolved in 500 ml. of methanol. (weight=about 20 g.) 45 g. of silica gel was added to this solution. The solution was evaporated to dryness in vacuo.

Workup

  1. customA reaction mixture was prepared
  2. additioncontaining the following ingredients
  3. additionthe reaction mixture was added to 500 ml

Sources & evidence

ORD record
ord-24fcbea78aeb44728c85dd8f96ff3e4e
Source dataset
uspto-grants-1985_11
Patent number
US04552888

Reaction notes

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