Methanesulfonyl chloride → HCID 12174535, compound

HRID 2095658Notes

Reaction equation

HRID 2095658 reaction equation
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1([O:6][S:8]([CH3:7])(=[O:10])=[O:9])[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 2814783-Cyclopenten-1-olHCID 516892Sodium Bicarbonate

Product 1

HCID 12174535HCID 12174535, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyclopentene-1-ol (9.00 g, 107 mmol) in dry methylene chloride (150 mL) was added TEA (23.0 mL, 160 mmol) followed by DMAP (100 mg). To this solution was added methanesulfonyl chloride (14.72 g, 128 mmol) at 10-20° C. slowly over 15 minutes and stirred overnight at room temperature. To the reaction mixture was added aqueous saturated NaHCO3 (50 mL) and stirred for 15 minutes at room temperature. The organic layer was separated, washed with water, followed by brine and dried over NaSO4. It was filtered and concentrated to give the title compound as an oil that was used without purification in the next reaction. 1H NMR (300 MHz, CDCl3): δ=5.72 (s, 2H), 5.38 (mc, 1H), 3.00 (s, 3H), 2.81-2.61 (m, 4H).

Workup

  1. stirringstirred for 15 minutes at room temperature
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over NaSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c835edfa74f9458a9867ddd8c7f891e2
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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