Cyclohexene oxide → HCID 67266608, compound

HRID 1698287Notes

Reaction equation

HRID 1698287 reaction equation
C(O)(C(F)(F)F)C(F)(F)F.[O:11]=[C:12]1[O:18][C@H:17]([C@H:19]([CH2:21][OH:22])[OH:20])[C:15]([OH:16])=[C:13]1[OH:14].[O:23]1[CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]12>C(#N)C>[OH:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]1[O:16][C:15]1[C@@H:17]([C@H:19]([CH2:21][OH:22])[OH:20])[O:18][C:12](=[O:11])[C:13]=1[OH:14]

Participants

5

Reactant 3

HCID 9246Cyclohexene oxideHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 54670067L-Ascorbic Acid

Product 1

HCID 67266608HCID 67266608, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Under an argon atmosphere, 4 ml of 1,1,1,3,3,3-hexafluoro isopropanol and 12 ml of acetonitrile were added to L-ascorbic acid (1.00 g), and further, 1,2-epoxycyclohexane (1.42 g) was added. The mixture was heated up to 70° C. and stirred for 36 hours, then, concentrated under reduced pressure, and 3.65 g of the resultant residue was subjected to silica gel column chromatography. Thereafter, it was eluted with chloroform/methanol/water(volume ratio:20/3/0.3) to obtain two elution fractions (first eluted fraction: 244 mg, later eluted fraction: 217 mg). Based on the measurement results of high resolution mass analysis, infrared absorption spectrum, 1H-NMR, 13C-NMR and specific optical rotation on the resultant elution fractions, it was confirmed that these are two 3-O-(2-hydroxycyclohexyl) ascorbic acids which are in mutual stereoisomerism and both of them are represented by the following structural formula.

Workup

  1. concentrationconcentrated under reduced pressure, and 3.65 g of the resultant residue
  2. washThereafter, it was eluted with chloroform/methanol/water(volume ratio:20/3/0.3)
  3. customto obtain
  4. washtwo elution fractions (first eluted fraction
  5. customresults of high resolution mass analysis
  6. customabsorption spectrum
  7. wash1H-NMR, 13C-NMR and specific optical rotation on the resultant elution fractions, it

Sources & evidence

ORD record
ord-53f89eba16c8430785dce04b52fb9b60
Source dataset
uspto-grants-2012_04
Patent number
US08163939B2

Reaction notes

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