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

HRID 882708Notes

Reaction equation

HRID 882708 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-52867257580c4af0bf082b8a3e028a37
Source dataset
uspto-grants-2012_08
Patent number
US08236786B2

Reaction notes

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