Methyl iodide → 2-Chloro-5-(methoxymethyl)pyridine

HRID 627710Notes

Reaction equation

HRID 627710 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][N:3]=1.[H-].[Na+].[CH3:12]I>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH3:12])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 177161(6-Chloropyridin-3-yl)methanol

Product 1

HCID 190109212-Chloro-5-(methoxymethyl)pyridineYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-hydroxymethylpyridine (1 g, 6.97 mmol) in THF (34.8 ml) was added sodium hydride (60% wt) (0.418 g, 10.45 mmol). The reaction was stirred for 10 minutes and treated with methyl iodide (0.653 ml, 10.45 mmol). The reaction was stirred at ambient temperature for 4 hrs. The reaction mixture was quenched with saturated NH4Cl and extracted with EtOAc. The organic portion was concentrated and purified in 10-40% EtOAc/Heptanes to give the title compound (880 mg, 5.58 mmol, 80% yield) as a tan solid. MS m/z=157.9 (M+H).

Workup

  1. stirringThe reaction was stirred at ambient temperature for 4 hrs
  2. customThe reaction mixture was quenched with saturated NH4Cl
  3. extractionextracted with EtOAc
  4. concentrationThe organic portion was concentrated
  5. custompurified in 10-40% EtOAc/Heptanes

Sources & evidence

ORD record
ord-1bb57140b8b84819bf0358fbc7831299
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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