Sulfuric Acid → HCID 67198831, compound

HRID 551713Notes

Reaction equation

HRID 551713 reaction equation
[CH:1]([C:3]1[CH2:4][C@H:5]2[C@@H:12]([CH:13]=1)[C:7]1(OCC[O:8]1)[CH2:6]2)=[CH2:2].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(#N)C.O>[CH:1]([C:3]1[CH2:4][C@H:5]2[C@@H:12]([CH:13]=1)[C:7](=[O:8])[CH2:6]2)=[CH2:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 67200490HCID 67200490, compound

Product 1

HCID 67198831HCID 67198831, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(±)-(1R,5S)-3-vinylspiro[bicyclo[3.2.0]hept-3-ene-6,2′-[1,3]dioxolane] (990 mg, 5.55 mmol) was dissolved in a mixed solvent of acetonitrile (16 mL) and water (7 mL). To the solution, 2 M sulfuric acid (2.60 mL) was added with stirring at room temperature. The mixture was stirred at room temperature for 7 hours, and the reaction solution was then neutralized by the addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the compound of interest was obtained as an oil substance (710 mg, 55%, Major/Minor=2/1) in the same way as in Example (11-e) from the obtained (1R,5S)-3-vinylbicyclo[3.2.0]hept-3-en-6-one.

Workup

  1. stirringThe mixture was stirred at room temperature for 7 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe residue was filtered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b966fd40720a457090cac4ad4b3cf4f6
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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