Triethylamine → 2-(5-Ethylpyridin-2-yl)ethyl methanesulfonate

HRID 1522799Notes

Reaction equation

HRID 1522799 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][OH:11])=[N:7][CH:8]=1)[CH3:2].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21])=[N:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 788945-Ethyl-2-pyridineethanol

Product 1

HCID 117702472-(5-Ethylpyridin-2-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(5-ethyl-pyridine-2-yl)-ethanol (25.34 g) and triethylamine (46.7 mL) in DCM (130 mL) at 0° C. under nitrogen was added methane sulfonyl chloride (15.56 mL), then the reaction mixture was allowed to warm to room temperature and stirred overnight. A further portion of methane sulfonyl chloride (3.88 mL) was added and the reaction stirred for 30 min. The reaction was diluted with DCM and washed with H2O and brine. The organic layer was dried (MgSO4) and the solution concentrated to give the title compound as a red oil (38.24 g). 1H NMR (400 MHz, CDCl3): δ 8.39 (d, J=2.2 Hz, 1H), 7.47 (dd, J=7.7, 2.3 Hz, 1H), 7.14 (d, J=7.7 Hz, 1H), 4.64 (t, J=6.5 Hz, 2H), 3.19 (t, J=6.5 Hz, 2H), 2.90 (s, 3H), 2.64 (q, J=7.6 Hz, 2H), 1.25 (t, J=7.6 Hz, 3H).

Workup

  1. stirringthe reaction stirred for 30 min
  2. washwashed with H2O and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-90dafa81432c4fddab69d4f376d66cbd
Source dataset
uspto-grants-2015_07
Patent number
US09078885B2

Reaction notes

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