Methyl iodide → HCID 68433293, compound

HRID 1867383Notes

Reaction equation

HRID 1867383 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[C:10]([CH2:16][OH:17])=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[H-].[Na+].I[CH3:23]>C1COCC1>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[C:10]([CH2:16][O:17][CH3:23])=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68435388HCID 68435388, compound

Product 1

HCID 68433293HCID 68433293, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.55 g (6.00 mmol) of [3-(4-Methoxy-benzyloxy)-6-methyl-pyridin-2-yl]-methanol in cold 10 ml THF (0° C.) was treated 30 min with 0.41 g (10.30 mmol) of NaH (55% in oil), then 0.43 ml (6.90 mmol) of iodomethane was added and the yellow suspension stirred 1 h. An extraction (water/CH2Cl2) and a chromatography (silica gel, AcOEt/n-n-heptane) delivered 1.41 g (86%) of the title compound as a yellow oil. MS: 274.3 (MH+).

Workup

  1. extractionAn extraction (water/CH2Cl2)

Sources & evidence

ORD record
ord-f050e49f6c2d4592a51f6e3f428e1fc3
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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