Triethylamine → 4-Pyridinepropanol, 4-methanesulfonate

HRID 1894386Notes

Reaction equation

HRID 1894386 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][OH:10])=[CH:3][CH:2]=1.C(N(CC)CC)C.[S:18](Cl)([CH3:21])(=[O:20])=[O:19]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][O:10][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 729234-Pyridinepropanol

Product 1

HCID 866300214-Pyridinepropanol, 4-methanesulfonateYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a round bottom flask was charged with 4-pyridinepropanol (5 g, 36.45mmol), triethylamine (5.7 mL, 72.9 mmol), methylene chloride (80 mL). The solution was cooled down to 0° C. and mesyl chloride (5.7 mL, 72.9 mmol) in methylene chloride (20 mL) was slowly added. The ice bath was removed, and the mixture was stirred at room temperature overnight before being concentrated. The residue was diluted with ethyl acetate, and the organic was washed with water (2×) and brine (1×). It was dried over anhydrous sodium sulfate and concentrated to give methanesulfonic acid 3-pyridin-4-yl-propyl ester as a dark oil (6.52 g).

Workup

  1. customThe ice bath was removed
  2. concentrationbefore being concentrated
  3. additionThe residue was diluted with ethyl acetate
  4. washthe organic was washed with water (2×) and brine (1×)
  5. dry with materialIt was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9a6fef2bea648e1ad061742373bb03d
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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