3,4-dihydro-2H-pyran → 1(1-Naphthyl)-1-(tetrahydropyran-2yloxy)-2-[2(p-toluenesulfonyloxy)ethoxy]ethane

HRID 362967Notes

Reaction equation

HRID 362967 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]1([CH:28]([OH:44])[CH2:29][O:30][CH2:31][CH2:32][O:33][S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:36])=[O:35])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1.[O:45]1[CH:50]=[CH:49][CH2:48][CH2:47][CH2:46]1>C(Cl)Cl>[C:18]1([CH:28]([O:44][CH:46]2[CH2:47][CH2:48][CH2:49][CH2:50][O:45]2)[CH2:29][O:30][CH2:31][CH2:32][O:33][S:34]([C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)(=[O:35])=[O:36])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 541300371(1Naphthyl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanol

Product 1

HCID 537184601(1-Naphthyl)-1-(tetrahydropyran-2yloxy)-2-[2(p-toluenesulfonyloxy)ethoxy]ethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.82 g of pyridinium p-toluenesulfonate was added to a solution of 6.3 g of 1-(1-naphthyl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanol and 2.97 ml of 3,4-dihydro-2H-pyran dissolved in 63 ml of methylene chloride at room temperature. The resulting mixture was stirred at the same temperature for 20 minutes and further at 35°-40° C. for 10 minutes. The reaction mixture was cooled, washed with water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: toluene/ethyl acetate=10/1) to obtain 7.53 g of colorless, oily 1-(1-naphthyl)-1-(tetrahydropyran-2-yloxy)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethane.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by column chromatography (eluant: toluene/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-f4952339fc0646d3b811fcbe2e5c6fc8
Source dataset
uspto-grants-1999_02
Patent number
US05872117

Reaction notes

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