Tetrahydropyran-2-methanol → HCID 18182313, compound

HRID 1359385Notes

Reaction equation

HRID 1359385 reaction equation
[H-].[Na+].[CH2:3]([C:10]1[C:15]([O:16][CH2:17][O:18][CH3:19])=[CH:14][CH:13]=[C:12](I)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][OH:28].[Cl-].[NH4+]>C(OCC)(=O)C>[CH2:3]([C:10]1[C:15]([O:16][CH2:17][O:18][CH3:19])=[CH:14][CH:13]=[C:12]([O:28][CH2:27][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][O:21]2)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 7524Tetrahydropyran-2-methanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 21942282HCID 21942282, compound

Product 1

HCID 18182313HCID 18182313, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Sodium hydride was added to a mixture of 456 mg of 2-benzyl-6-iodo-3-(methoxymethyloxy)pyridine, 122 mg of cuprous iodide and 3 ml of tetrahydropyran-2-methanol, followed by stirring at 90° C. for 3 hours. An aqueous ammonium chloride solution and ethyl acetate were added to the reaction solution, followed by stirring at room temperature for one hour. Then, 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 15% ethyl acetate/hexane, to give 383 mg of the target compound.

Workup

  1. stirringby stirring at room temperature for one hour
  2. washThen, the 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-3a3a20c3160140a389f7afc23408ed39
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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