2,2-Dimethoxypropane → HCID 13672387, compound

HRID 542552Notes

Reaction equation

HRID 542552 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]CC=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[CH3:47][O:48][C:49]([O:52][CH3:53])([CH3:51])C>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][CH2:51][CH:49]([O:48][CH3:47])[O:52][CH3:53])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 13672382HCID 13672382, compound

Product 1

HCID 13672387HCID 13672387, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In this example, 5 m moles of 4-benzyloxy-2-(10-formyldecyl) quinoline-N-oxide is dissolved in dichloromethane, and a catalytic amount of D-camphorsulfonic acid and a large excess of 2,2-dimethoxypropane are added thereto. The mixture is stirred at room temperature for 3 hours. After the reaction, the reaction solution is washed with an aqueous saturated sodium hydrogen carbonate solution, and then with water, and dried over anhydrous sodium sulfate. After removal of the solvent by distillation, the residue is purified by silica gel column procedure, whereby the captioned compound is obtained as a colorless oily substance (yield: 70.6%).

Workup

  1. customAfter the reaction
  2. washthe reaction solution is washed with an aqueous saturated sodium hydrogen carbonate solution
  3. dry with materialwith water, and dried over anhydrous sodium sulfate
  4. customAfter removal of the solvent
  5. distillationby distillation
  6. customthe residue is purified by silica gel column procedure, whereby the captioned compound
  7. customis obtained as a colorless oily substance (yield: 70.6%)

Sources & evidence

ORD record
ord-b52b1c388b574fe783f011c9c11ba84b
Source dataset
uspto-grants-1987_04
Patent number
US04657916

Reaction notes

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