Pyridine → HCID 12174535, compound

HRID 222213Notes

Reaction equation

HRID 222213 reaction equation
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.N1C=CC=CC=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl>[CH3:13][S:14]([O:6][CH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2×HCID 2814783-Cyclopenten-1-ol

Product 1

HCID 12174535HCID 12174535, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

3-Cyclopentene-1-ol (0.500 g, 5.94 mmol) was stirred in DCM (95 mL). Pyridine (2.40 mL), N,N-dimethylaminopyridine (0.10 g, 1.00 mmol) and methanesulfonyl chloride (0.690 mL, 8.92 mmol) were added, and the reaction mixture was stirred at 35° C. for 4 h. N,N-Dimethylaminopyridine (0.14 g, 1.2 mmol) and methanesulfonyl chloride (0.69 mL, 8.92 mmol) were added, and the reaction was stirred overnight. TLC indicated complete conversion. The reaction mixture was cooled and concentrated. The residue was purified by silica gel chromatography, eluting with DCM, to afford the title compound as a clear oil (0.660 g, 68%).

Workup

  1. stirringthe reaction was stirred overnight
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with DCM

Sources & evidence

ORD record
ord-b980014275ae42bab0211f78cfe46a2a
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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