Triethylamine → Methyl 6-((methylsulfonyloxy)methyl)picolinate

HRID 408875

Reaction equation

HRID 408875 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=1.[CH2:12](N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([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:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 225044906-(Hydroxymethyl)picolinate

Product 1

HCID 54451634Methyl 6-((methylsulfonyloxy)methyl)picolinateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(Hydroxymethyl)picolinate (200 mg, 1.196 mmol) and triethylamine (363 mg, 3.588 mmol, 0.5 mL) were combined and stirred at 0° C. in dichloromethane (2 mL). Methanesulfonyl chloride (206 mg, 1.794 mmol) was added and the reaction allowed to warm to room temperature over 1 hour. The reaction was washed with water, dried over sodium sulfate and concentrated under vacuum to afford the title compound (293 mg). MS (ESI) m/z 246.3 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-c4f5d6d678e345d8ae3d2e892499c2cd
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Linked notes

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