Dichloromethane → HCID 18182425, compound

HRID 1359332Notes

Reaction equation

HRID 1359332 reaction equation
CS(Cl)(=O)=O.[CH2:6]([C:13]1[C:18]([O:19][CH2:20][O:21][CH3:22])=[CH:17][CH:16]=[C:15]([C:23]2(O)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.ClCCl>C(OCC)(=O)C.O>[CH2:6]([C:13]1[C:18]([O:19][CH2:20][O:21][CH3:22])=[CH:17][CH:16]=[C:15]([C:23]2[CH2:28][CH2:27][O:26][CH2:25][CH:24]=2)[N:14]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18182513HCID 18182513, compound

Product 1

HCID 18182425HCID 18182425, compoundYield 36.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

716 μl of methanesulfonyl chloride was added dropwise into a mixture of 1.02 g of 2-benzyl-6-(4-hydroxytetrahydro-4H-pyran-4-yl)-3-methoxymethyloxypyridine (Example 60a), 1.72 ml of triethylamine and 10 ml of dichloromethane under ice-cooling. After stirring at room temperature overnight, water and ethyl acetate were 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 20% ethyl acetate/hexane, to give 355 mg of the target compound.

Workup

  1. temperaturecooling
  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-fba1a51d958d4de280c51b78d61862b2
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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