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

HRID 1889722ノート

反応式

HRID 1889722 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

HCID 54451634Methyl 6-((methylsulfonyloxy)methyl)picolinate収率 110.5%

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-1926a0445d764d8ebffc2b8ea1b741b6
出典データセット
uspto-grants-2013_08
特許番号
US08501992B2

反応ノート

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