Water → HCID 22708771, compound

HRID 547886Notes

Reaction equation

HRID 547886 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>C(Cl)Cl>[CH3:17][S:18]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 76752-(2-Hydroxyethyl)pyridineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 22708771HCID 22708771, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0.2 M solution of 2-(2-hydroxyethyl)pyridine (4.5 mmol) in methylene chloride is added triethylamine (24 mmol), followed by methanesulfonyl chloride (4.8 mmol.) The resulting mixture is stirred at room temperature overnight. The mixture is then poured into water and extracted with methylene chloride. The organic extracts are combined, washed with NaHCO3 (sat), and then 1M aq. HCl. The acidic aqueous extracts are neutralized with NaHCO3 (sat) and then extracted with methylene chloride. The organic extracts were combined, dried (MgSO4), filtered, and concentrated to afford the desired product (1).

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with NaHCO3 (sat)
  3. extractionextracted with methylene chloride
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dcebb4af51824c3f8ab067361e2cddfa
Source dataset
uspto-grants-2011_05
Patent number
US07939657B2

Reaction notes

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