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

HRID 912523Notes

Reaction equation

HRID 912523 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]1[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][C:8]1[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][CH:9]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

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

Product 1

HCID 54451634Methyl 6-((methylsulfonyloxy)methyl)picolinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulphonyl chloride (0.28 ml) was added at 0° C. to a solution of methyl 6-hydroxymethylpicolinate (500 mg), TEA (0.5 ml) in DCM (5 ml). The mixture was stirred at rt for 1 hour, then diluted with DCM (50 ml) and washed with water (2×30 ml). Organic layer dried, solvent removed under vacuum to give expected product methyl 6-((methylsulfonyloxy)methyl)picolinate (770 mg). 1H NMR (CDCl3) δ: 8.11 (d, 1H), 7.93 (t, 1H), 7.70 (d, 1H), 5.44 (s, 2H), 4.01 (s, 3H), 3.16 (s, 3H).

Workup

  1. washwashed with water (2×30 ml)
  2. customOrganic layer dried
  3. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-5046f021efa844da9cd32ecd5c24e81f
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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