3,4-dihydro-2H-pyran → 2-[1-(2-p-Toluenesulphonyloxyethyl)cyclopropyloxy]tetrahydro-4H-pyran

HRID 1591050Notes

Reaction equation

HRID 1591050 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][CH2:12][C:13]2([OH:16])[CH2:15][CH2:14]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[C:1]1([CH3:17])[CH:2]=[CH:3][C:4]([S:7]([O:10][CH2:11][CH2:12][C:13]2([O:16][CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][O:18]3)[CH2:14][CH2:15]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 197661081-(2-p-Toluenesulphonyloxyethyl)cyclopropanol

Product 1

HCID 197661232-[1-(2-p-Toluenesulphonyloxyethyl)cyclopropyloxy]tetrahydro-4H-pyran

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-p-toluenesulphonyloxyethyl)cyclopropanol (an intermediate in Preparation 2) (1.30 g) in dichloromethane (15 ml) at room temperature was added dihydropyran (0.88 g, 95%) and pyridinium p-toluenesulfonate (0.1 g). After 5 hours, the reaction solution was diluted with ether (70 ml) and extracted consecutively with water, 5% sodium hydrogen carbonate solution, and brine. After drying and removal of the solvent in vacuo, the product was purified by chromatography (50 g silica gel; 30% ether in petroleum ether as solvent) followed by recrystallisation from hexane to give the title compound as plates, m.p. 56°-57° C. (Found C, 59.99; H, 7.13; S 9.37. C17H24O5S requires C, 59.98; H, 7.11; S 9.42%), δ (100 MHz) 0.5 (2H, m), 0.85 (2H, m), 1.2-2.4 (8H, m), 3.1-3.9 (4H, m), 4.55 (1H, m), 7.6 (3H, m), 7.9 (2H, m).

Workup

  1. extractionextracted consecutively with water, 5% sodium hydrogen carbonate solution, and brine
  2. customAfter drying
  3. customremoval of the solvent in vacuo
  4. customthe product was purified by chromatography (50 g silica gel; 30% ether in petroleum ether as solvent)
  5. customfollowed by recrystallisation from hexane

Sources & evidence

ORD record
ord-6908fa66cd6441b28a87829cdd58196f
Source dataset
uspto-grants-1993_04
Patent number
US05206229

Reaction notes

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