Triethylamine → 4-(Methanesulfonyl)oxytetrahydrothiopyran

HRID 2270104Notes

Reaction equation

HRID 2270104 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.[CH3:8][S:9](Cl)(=[O:11])=[O:10].C(N(CC)CC)C>C(Cl)Cl>[CH3:8][S:9]([O:1][CH:2]1[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576296Tetrahydro-2H-thiopyran-4-ol

Product 1

HCID 124202654-(Methanesulfonyl)oxytetrahydrothiopyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 300 ml methylene chloride solution of 14.6 g (0.12 mol) of 4-hydroxytetrahydrothiopyran, 11.5 ml (0.15 mol) of methanesulfonyl chloride and 25.8 ml (0.19 mol) of triethylamine were added at 0° C. and stirred at room temperature for 1 hour. The reaction mixture was diluted with methylene chloride (100 ml) and successively washing with water (100 ml) and saturated saline (100 ml), followed by drying over anhydrous sodium sulfate. The solvent was then distilled off under vacuum to obtain 24.5 g (quant.) of the above-identified compound as a slightly brown crystal.

Workup

  1. washsuccessively washing with water (100 ml) and saturated saline (100 ml)
  2. dry with materialby drying over anhydrous sodium sulfate
  3. distillationThe solvent was then distilled off under vacuum
  4. customto obtain 24.5 g (quant.) of the above-identified compound as a slightly brown crystal

Sources & evidence

ORD record
ord-9332a5eff53840b7b73ba6a6f266a355
Source dataset
uspto-grants-2001_12
Patent number
US06331548B1

Reaction notes

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