Tetrahydrofuran → HCID 67200490, compound

HRID 551712Notes

Reaction equation

HRID 551712 reaction equation
[Cl-].[Li+].[CH2:3]([Sn](CCCC)(CCCC)C=C)[CH2:4]CC.O1CCCC1.FC(F)(F)S(O[C:29]1[CH2:30][C@H:31]2[C@@H:38]([CH:39]=1)[C:33]1([O:37][CH2:36][CH2:35][O:34]1)[CH2:32]2)(=O)=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH:3]([C:29]1[CH2:30][C@H:31]2[C@@H:38]([CH:39]=1)[C:33]1([O:37][CH2:36][CH2:35][O:34]1)[CH2:32]2)=[CH2:4]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 86646167HCID 86646167, compound

Product 1

HCID 67200490HCID 67200490, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Lithium chloride (1.97 g, 46.4 mmol), tetrakis(triphenylphosphine)palladium (0) (0.36 g, 0.31 mmol), and tributyl(vinyl)tin (2.47 mL, 8.50 mmol) were added to a tetrahydrofuran solution (60 mL) of (±)-(1R,5S)-spiro[bicyclo[3.2.0]hept-3-ene-6,2′-[1,3]dioxolan]-3-yl trifluoromethanesulfonate (2.32 g, 7.73 mmol). The mixture was heated to reflux for 2 hours, and water was then added to the reaction solution, followed by extraction with diethyl ether. 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 obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (990 mg, 72%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. extractionfollowed by extraction with diethyl ether
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe residue was filtered
  7. concentrationconcentrated under reduced pressure
  8. customThen, the obtained crude product
  9. customwas purified by silica gel column chromatography
  10. customto obtain the compound of interest as an oil substance (990 mg, 72%)

Sources & evidence

ORD record
ord-19c6c023a7dd489aa650eb363d4f782c
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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