Triethylamine → (2-Chloropyridin-4-yl)methyl methanesulfonate

HRID 1467962

Reaction equation

HRID 1467962 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 7062237(2-Chloropyridin-4-yl)methanol

Product 1

HCID 53436764(2-Chloropyridin-4-yl)methyl methanesulfonateYield 68.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2-chloropyridin-4-yl)methanol (0.500 g, 3.496 mmol) in dichloromethane (15 mL), triethylamine (0.424 g, 4.195 mmol) and methanesulfonylchloride (0.440 g, 3.846 mmol) were added at 0° C. and stirred at room temperature for 2-3 h. The reaction was quenched with water and extracted with dichloromethane. The organic layer was concentrated in vacuo to give (2-chloropyridin-4-yl)methyl methanesulfonate (0.530 g, 68%); MS: 221.9 (M+1).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-dbe6dcafa19e4fc0b55dd62ddede6b56
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Linked notes

Loading…