3,4-dihydro-2H-pyran → HCID 70607943, compound

HRID 2163167Notes

Reaction equation

HRID 2163167 reaction equation
[OH:1][C@@H:2]1[CH2:6][C@@H:5]([OH:7])[CH:4]=[CH:3]1.[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1>C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:1][C@H:2]1[CH:3]=[CH:4][C@H:5]([OH:7])[CH2:6]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 12201273HCID 12201273, compound

Product 1

HCID 70607943HCID 70607943, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

Ten milligrams of (R)-trans-3,5-dihydroxycyclopent-1-ene and 8 milligrams of dihydropyran were stirred at room temperature for 24 hours in 1.0 milliliter of methylene chloride in the presence of 0.1 milligram of p-toluenesulfonic acid. The organic solution was first washed with an aqueous sodium bicarbonate solution and then with an aqueous sodium chloride solution followed by drying with magnesium sulfate and thereafter distilling off the solvent under reduced pressure to obtain a crude product. This product was purified by thin-layer chromatography (n-hexane:ethyl acetate = 6:4), and 11 milligrams (60%) of (R)-trans-5-tetrahydropyranyloxycyclopent-1-en-3-ol was obtained.

Workup

  1. washThe organic solution was first washed with an aqueous sodium bicarbonate solution
  2. dry with materialby drying with magnesium sulfate
  3. distillationdistilling off the solvent under reduced pressure
  4. customto obtain a crude product
  5. customThis product was purified by thin-layer chromatography (n-hexane:ethyl acetate = 6:4)

Sources & evidence

ORD record
ord-d51c9c3f7da440e2bb17938826856095
Source dataset
uspto-grants-1979_01
Patent number
US04132726

Reaction notes

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