Pyridine → HCID 86607685, compound

HRID 1432817Notes

Reaction equation

HRID 1432817 reaction equation
[CH:1]1(O)[CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[F:12][C:13]([F:26])([F:25])[S:14]([O:17]S(C(F)(F)F)(=O)=O)(=[O:16])=[O:15].[C:27]1([S:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl.CCCCC>[F:12][C:13]([F:26])([F:25])[S:14]([O-:17])(=[O:16])=[O:15].[CH:1]1([S+:33]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8766Diphenyl sulfideHCID 67749Trifluoromethanesulfonic anhydrideHCID 76218Cyclobutanol

Product 1

HCID 86607685HCID 86607685, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003PentaneSolvent2×

Procedure

A solution of cyclobutanol (1.00 g, 13.9 mmol) in 25 ml of DCM was chilled to −20° C. and dry pyridine (1.35 ml, 16.6 mmol) added, followed by trifluoromethanesulfonic anhydride (2.33 ml, 13.9 mmol) (in 5 ml of DCM). The solution was allowed to warm to room temperature over 1 hr. Pentane (40 mL) was added and the resulting mixture shaken and filtered. The filtrate was concentrated under reduced pressure with a room temperature bath until all volatile solvents were removed. The residual oil was chilled to −20° C. and diphenylsulfane (10.2 ml, 61.0 mmol) added. The mixture was stirred at 25° C. for 20 hr, warmed to 45° C. for 30 minutes and cooled to room temperature. Pentane was added, the solution shaken and the resulting solid collected by vacuum filtration to give cyclobutyldiphenylsulfonium trifluoromethanesulfonate (1.82 g, 4.86 mmol, 35.0%). MS: m/z (ES+): 241 [C16H17S]+. 1H NMR (D6-DMSO): δ 8.10 (dt, 4H, J1=7.8, J2=3.1), 7.84-7.72 (m, 6H), 5.90-5.78 (m, 1H), 5.15 (ddd, 2H, J1=14.9, J2=10.3, J3=1.4), 4.48 (t, 2H, J=14.2), 2.45 (dd, 2H, J1=13.8, J2=7.1).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure with a room temperature bath until all volatile solvents
  3. customwere removed
  4. temperatureThe residual oil was chilled to −20° C.
  5. stirringThe mixture was stirred at 25° C. for 20 hr
  6. temperaturewarmed to 45° C. for 30 minutes
  7. temperaturecooled to room temperature
  8. stirringthe solution shaken
  9. filtrationthe resulting solid collected by vacuum filtration

Sources & evidence

ORD record
ord-bbad2d8bdace491c98a664fa1cf4fd45
Source dataset
uspto-grants-2009_11
Patent number
US07612106B2

Reaction notes

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