Pyridine → HCID 86607685, compound

HRID 1295083Notes

Reaction equation

HRID 1295083 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-50df1125d47f4e8a9275b5112351e1dc
Source dataset
uspto-grants-2007_07
Patent number
US07241792B2

Reaction notes

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