Methanesulfonyl chloride → Methyl 6-((methylsulfonyloxy)methyl)picolinate

HRID 1889722Notes

Reaction equation

HRID 1889722 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:13][S:14]([O:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1)(=[O:16])=[O:15]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11513809Methyl 6-(hydroxymethyl)picolinate

Product 1

HCID 54451634Methyl 6-((methylsulfonyloxy)methyl)picolinateYield 110.5%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 6-(hydroxymethyl)picolinate (2.6 g, 15.5 mmol) in CH2Cl2 (15 mL) were added methanesulfonyl chloride (1.81 mL, 23.3 mmol) and TEA (5.42 mL, 38.9 mmol) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1 h and diluted with CHCl3 and saturated aqueous NaHCO3 solution. The organic layer was separated, washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated to give the desired compound (4.2 g, 85%) as a brown oil. 1H NMR (CDCl3) δ 8.15 (d, J=8.0 Hz, 1H), 7.96 (t, J=8.0 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 5.46 (s, 2H), 4.04 (s, 3H), 3.20 (s, 3H). MS (ESI): 246.1 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1926a0445d764d8ebffc2b8ea1b741b6
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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