3,4-dihydro-2H-pyran → HCID 10986966, compound

HRID 2163168Notes

Reaction equation

HRID 2163168 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 11274971HCID 11274971, compound

Product 1

HCID 10986966HCID 10986966, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

Ten milligrams of (S)-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. Next, the organic solution was washed with an aqueous sodium bicarbonate solution and then with an aqueous sodium chloride solution, after which it was dried with anhydrous magnesium sulfate followed by distilling off the solvent under reduced pressure. When the resulting crude product was purified by thin-layer chromatography (n-hexane:ethyl acetate = 6:4), 10 milligrams (54%) of (S)-trans-5-tetrahydropyranyloxycyclopent-1-en-3-ol was obtained. The IR and NMR of this product was in complete agreement with those of the product obtained in Example 36.

Workup

  1. washNext, the organic solution was washed with an aqueous sodium bicarbonate solution
  2. dry with materialwith an aqueous sodium chloride solution, after which it was dried with anhydrous magnesium sulfate
  3. distillationby distilling off the solvent under reduced pressure
  4. customWhen the resulting crude product was purified by thin-layer chromatography (n-hexane:ethyl acetate = 6:4)

Sources & evidence

ORD record
ord-575bc7cbf04641e69fa689e06a9db721
Source dataset
uspto-grants-1979_01
Patent number
US04132726

Reaction notes

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