Triethylamine → 1-(Pyridin-2-yl)ethyl methanesulfonate

HRID 1592520Notes

Reaction equation

HRID 1592520 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([OH:9])[CH3:8].CCN(CC)CC.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([O:9][S:18]([CH3:17])(=[O:20])=[O:19])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86784alpha-Methyl-2-pyridinemethanol

Product 1

HCID 576559771-(Pyridin-2-yl)ethyl methanesulfonateYield 105.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-pyridin-2-yl-ethanol (156 mg, 1.27 mmol) (Mandal, S. K. et al. J. Org. Chem. 2003, 68, 4600-4603) and Et3N (0.27 mL, 1.94 mmol) in CH2Cl2 (5 mL) was added methanesulphonyl chloride (0.11 mL, 1.29 mmol) and the solution was stirred for 70 minutes. The solution was diluted with CH2Cl2 (20 mL) and washed with saturated aqueous NaHCO3 (2×15 mL) and brine (1×15 mL). The combined aqueous phase was extracted with CH2Cl2 (1×15 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated under reduced pressure to give crude methanesulphonic acid 1-pyridin-2-yl-ethyl ester as a yellow oil (269 mg, 100%). 1H NMR (CDCl3) δ 1.77 (d, 3H, J=6.6 Hz), 2.94 (s, 3H), 5.79 (q, 1H, J=6.6 Hz), 7.28 (ddd, 1H, J=7.4, 7.1, 1.3 Hz), 7.47 (d, 1H, J=7.9 Hz), 7.76 (td, 1H, J=7.6, 1.7 Hz), 8.61 (d, 1H, J=4.9 Hz).

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×15 mL) and brine (1×15 mL)
  2. extractionThe combined aqueous phase was extracted with CH2Cl2 (1×15 mL)
  3. dry with materialThe combined organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f80dbdfd159e41b6926756b1241dbb23
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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