Methyl triflate → 4-Acetylthio-1-methyl-tetrahydrothiopyraniumtriflate

HRID 978601Notes

Reaction equation

HRID 978601 reaction equation
[C:1]([S:4][CH:5]1[CH2:10][CH2:9][S:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].[CH3:11][O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14]>ClCCl>[F:17][C:16]([F:19])([F:18])[S:13]([O-:15])(=[O:14])=[O:12].[C:1]([S:4][CH:5]1[CH2:10][CH2:9][S+:8]([CH3:11])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 138537674-Methylcarbonylthiothiane

Product 1

HCID 867414894-Acetylthio-1-methyl-tetrahydrothiopyraniumtriflateYield 103.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (5° C.) solution of 4-acetylmercaptotetrahydrothiopyran (1.91 g, 10.9 mmol) in dichloromethane (20 mL) was added methyltrifluoromethanesulfonate (1.3 mL, 11.5 mmol) dropwise over 30 minutes. The solvent was removed in vacuo to give 3.85 g (>100%) of the title compound as an oil which was used as such: 1Hmr (D2O) δ: 2.14-3.79 (m, 8H, ring protons), 2.39 (s, 3H, COCH3), 2.93 (s, 3H, SCH3) and 5.46 ppm (s, 1H, CHS).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9bfb60c66c4547c2966dd1b4d74f307e
Source dataset
uspto-grants-1987_05
Patent number
US04665169

Reaction notes

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