Triethylamine → Methyl 2-((methylsulfonyloxy)methyl)isonicotinate

HRID 408879Notes

Reaction equation

HRID 408879 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[CH3:20][S:21]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13276248Methyl 2-(hydroxymethyl)pyridine-4-carboxylate

Product 1

HCID 86661353Methyl 2-((methylsulfonyloxy)methyl)isonicotinateYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(hydroxymethyl)isonicotinate (3.17 mmol, 0.530 g) and triethylamine (9.51 mmol, 1.322 mL, 0.963 g) were stirred in dichloromethane (20 mL) at 0° C. Methanesulfonyl chloride (4.76 mmol, 0.368 mL, 0.545 g) was added dropwise and the reaction stirred at room temperature for 1 hour. The reaction mixture was washed with water, dried over sodium sulfate and concentrated under vacuum to afford the title compound (686 mg). MS (ESI) m/z 246.4 [M+H]+

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cb938becee4f4cf3b5fe9f18ce0635b3
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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