Methanesulfonyl chloride → (S)-3-Fluoroheptyl Methanesulfonate

HRID 2209375Notes

Reaction equation

HRID 2209375 reaction equation
[F:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][CH2:4][OH:5].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1>[CH3:10][S:11]([O:5][CH2:4][CH2:3][C@@H:2]([F:1])[CH2:6][CH2:7][CH2:8][CH3:9])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54122660(S)-3-fluoroheptanol

Product 1

HCID 22850589(S)-3-Fluoroheptyl MethanesulfonateYield 93.18%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 100 ml flask were added 8.7 g of (S)-3-fluoroheptanol and 21.5 g of pyridine under a nitrogen atmosphere, and the solution was kept at 5° to 10° C. To the solution was added dropwise 7.5 g of methanesulfonyl chloride over 30 minutes, followed by stirring at 15° C. or less for 5 hours. The reaction mixture was poured into 200 ml of ice-water and extracted with ethyl acetate. The organic layer was washed successively with a diluted hydrochloric aqueous solution and water, dried over magnesium sulfate, and the solvent was removed by distillation at 30° C. or lower to obtain 12.7 g (yield=93.18%) of the titled compound. NMR (ppm): 0.92 (3H, t, J=7.1 Hz), 1.35-1.8 (6H, m), 2.03 (2H, m), 3.02 (3H, s), 4.37 (1H, t, J=6.2 Hz), 4.65 (2H, m)

Workup

  1. customwas kept at 5° to 10° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with a diluted hydrochloric aqueous solution and water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed by distillation at 30° C.

Sources & evidence

ORD record
ord-5c5d88c401fd4335b76829cf295258c1
Source dataset
uspto-grants-1995_10
Patent number
US05454976

Reaction notes

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