3,4-dihydro-2H-pyran → HCID 13672381, compound

HRID 542548Notes

Reaction equation

HRID 542548 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N+:12]([O-:19])=[C:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[C:33]1(C)[C:37]2(CS(O)(=O)=O)[C:38](C[CH:34]1[CH2:35]C2)=[O:39].O1C=CCCC1>ClCCl>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N+:12]([O-:19])=[C:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][CH:38]2[CH2:37][CH2:33][CH2:34][CH2:35][O:39]2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 13672378HCID 13672378, compound

Product 1

HCID 13672381HCID 13672381, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In this example, 5 m moles of 4-benzyloxy-2-(11-hydroxyundecyl)-quinoline-N-oxide is dissolved in dichloromethane, and a catalytic amount of D-camphorsulfonic acid and 6 m moles of 2,3-dihydropyran are added thereto. The mixture is stirred at room temperature for 3 hours. Then, the reaction solution is washed with an aqueous sodium hydrogen carbonate solution and then with water, and dried over anhydrous sodium sulfate. The solvent is removed therefrom by distillation, and the residue is purified by silica gel column procedure, whereby the cationed compound is obtained as a colorless oily substance (yield: 82.3%).

Workup

  1. washThen, the reaction solution is washed with an aqueous sodium hydrogen carbonate solution
  2. dry with materialwith water, and dried over anhydrous sodium sulfate
  3. customThe solvent is removed
  4. distillationby distillation
  5. customthe residue is purified by silica gel column procedure, whereby the cationed compound
  6. customis obtained as a colorless oily substance (yield: 82.3%)

Sources & evidence

ORD record
ord-6d5c18019d814f64ad165299acea7441
Source dataset
uspto-grants-1987_04
Patent number
US04657916

Reaction notes

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