Methanesulfonyl chloride → HCID 22273259, compound

HRID 2200588Notes

Reaction equation

HRID 2200588 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5]1.[CH3:10][S:11](Cl)(=[O:13])=[O:12]>ClCCl>[CH3:10][S:11]([O:1][CH2:2][CH2:3][C:4]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 141019991-(2-Hydroxyethyl)cyclopentan-1-ol

Product 1

HCID 22273259HCID 22273259, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-hydroxyethyl)cyclopentanol (19 0 mg, 1.46 mmol) in dry dichloromethane (2 mL) was added methanesulfonyl chloride (200.3 mg, 1.75 mmol) dropwise at 0° C., followed by TEA (295 mg, 2.92 mmol). Then the mixture was stirred at room temperature 1 h. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product (50 mg, 31.1% yield), which was used without purification.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3658ae00bf7f4c9096036305a6549986
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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