2-Butyloxirane → HCID 67266629, compound

HRID 1698286Notes

Reaction equation

HRID 1698286 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].[O:13]1[CH:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14]1>CN(C=O)C>[OH:13][CH:15]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14][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]

Participants

4

Reactant 2

HCID 150362-ButyloxiraneHCID 54670067L-Ascorbic Acid

Product 1

HCID 67266629HCID 67266629, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, 30 ml of DMF was added to L-ascorbic acid (5.00 g), and further, 1,2-epoxyhexane (3.45 g) was added thereto. The mixture was heated up to 80° C. and stirred for 24 hours, then, extracted with ethyl acetate. The extracted liquid was dried over anhydrous sodium sulfate, then, concentrated under reduced pressure. Thereafter, 7.56 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-(2-hydroxyhexyl) ascorbic acid (1.93 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracted liquid was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washElution
  5. concentrationwas performed with chloroform/methanol/water(volume ratio:20/3/0.3), and concentration

Sources & evidence

ORD record
ord-322637751c984cb381227710ca7a1553
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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