Sulfuric Acid → HCID 90431901, compound

HRID 929434Notes

Reaction equation

HRID 929434 reaction equation
[CH3:1][Mg]Br.[CH3:4][C@:5]1([CH2:16][CH:17]=[O:18])[CH2:7][C@H:6]1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9].S(=O)(=O)(O)O>O1CCCC1>[CH3:4][C@:5]1([CH2:16][CH:17]([OH:18])[CH3:1])[CH2:7][C@H:6]1[CH:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 90431831HCID 90431831, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 90431901HCID 90431901, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, methyl magnesium bromide (0.97 mol/L tetrahydrofuran solution, 3.0 ml, 2.9 mmol) was placed into a 30-ml flask equipped with a stirring apparatus, a dropping funnel, and a thermometer. In the dropping funnel, 2-[(1R*,2S*)-1-methyl-2-(1-phenylethyl)cyclopropyl]acetaldehyde (a diastereomer mixture with a component ratio of 1:2, 0.20 g, 0.99 mmol) and tetrahydrofuran (1 ml) were placed, and added dropwise in 5 minutes, with the temperature kept at 20° C. At the same temperature, the mixture was stirred for 30 minutes. Next, a 5% aqueous sulfuric acid solution (2.9 g) was added. After stirring for 10 minutes, the aqueous layer was separated, and the organic layer was washed twice with water (2 ml). The solvent was recovered under reduced pressure to obtain a condensed residue. The results of a GC analysis showed that the condensed residue was a mixture of four isomers. This residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:2). Thus, a component (0.016 g, 0.07 mmol, 7% yield) with the longest retention time in the GC analysis was obtained. Results of evaluation based on gas chromatography-olfactometry (GC-O) showed that this component was a component having the lowest odor threshold, among the 4 isomers.

Workup

  1. customequipped with a stirring apparatus, a dropping funnel
  2. additionadded dropwise in 5 minutes, with the temperature
  3. customkept at 20° C
  4. stirringAfter stirring for 10 minutes
  5. customthe aqueous layer was separated
  6. washthe organic layer was washed twice with water (2 ml)
  7. customThe solvent was recovered under reduced pressure
  8. customto obtain a condensed residue
  9. customThe results of a GC analysis
  10. additiona mixture of four isomers
  11. customThis residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:2)
  12. customThus, a component (0.016 g, 0.07 mmol, 7% yield) with the longest retention time in the GC analysis was obtained
  13. customResults of evaluation

Sources & evidence

ORD record
ord-6aea65d74d5646aab96f725df38c0607
Source dataset
uspto-grants-2016_03
Patent number
US09296675B2

Reaction notes

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