3,4-dihydro-2H-pyran → 1-(Benzo[b]thiophen-5-yl)-1-(2-tetrahydropyranyloxy)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethane

HRID 976546Notes

Reaction equation

HRID 976546 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[S:18]1[CH:22]=[CH:21][C:20]2[CH:23]=[C:24]([CH:27]([OH:43])[CH2:28][O:29][CH2:30][CH2:31][O:32][S:33]([C:36]3[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:25]=[CH:26][C:19]1=2.[O:44]1[CH:49]=[CH:48][CH2:47][CH2:46][CH2:45]1>C(Cl)Cl>[S:18]1[CH:22]=[CH:21][C:20]2[CH:23]=[C:24]([CH:27]([O:43][CH:45]3[CH2:46][CH2:47][CH2:48][CH2:49][O:44]3)[CH2:28][O:29][CH2:30][CH2:31][O:32][S:33]([C:36]3[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=3)(=[O:35])=[O:34])[CH:25]=[CH:26][C:19]1=2

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 536544561-(Benzo[b]thiophen-5-yl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanol

Product 1

HCID 537989451-(Benzo[b]thiophen-5-yl)-1-(2-tetrahydropyranyloxy)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.97 g of pyridinium p-toluenesulfonate was added, at room temperature, to a solution of 7.6 g of 1-(benzo[b]thiophen-5-yl)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethanol and 3.5 ml of 3,4-dihydro-2H-pyran dissolved in 40 ml of methylene chloride. The mixture was stirred at the same temperature for 20 minutes and further at 40 to 45 for 30 minutes. The reaction mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 8.7 g of colorless, oily 1-(benzo[b]thiophen-5-yl)-1-(2-tetrahydropyranyloxy)-2-[2-(p-toluenesulfonyloxy)ethoxy]ethane.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-70d77bc5b76045ec9b2a74512abf2b30
Source dataset
uspto-grants-1997_03
Patent number
US05612381

Reaction notes

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