Dichloromethane → HCID 18182416, compound

HRID 1359328Notes

Reaction equation

HRID 1359328 reaction equation
[CH2:1]([C:8]1[C:13]([O:14]COC)=[CH:12][CH:11]=[C:10]([C:18]2([OH:24])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:1]([C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([C:18]2([OH:24])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 18182513HCID 18182513, compound

Product 1

HCID 18182416HCID 18182416, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of 377 mg of 2-benzyl-6-(4-hydroxytetrahydro-4H-pyran-4-yl)-3-methoxymethyloxypyridine, 2 ml of dichloromethane and 2 ml of trifluoroacetic acid was stirred at room temperature overnight. The reaction solution was neutralized by an aqueous sodium bicarbonate solution, and ethyl acetate was added thereto. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 60% ethyl acetate/hexane, to give 241 mg of the target compound.

Workup

  1. additionwas added
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-8c5a4f4b9f7d4905b87cc5b40ef1a72c
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

Loading…