Pyridine → n-Pentyltriflate

HRID 1944513Notes

Reaction equation

HRID 1944513 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)CCCC.[S:13]([O:20]S(C(F)(F)F)(=O)=O)([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14]>>[CH2:2]([O:20][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 3

HCID 1049PyridineHCID 62761-PentanolHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 10987782n-Pentyltriflate

Procedure

To a nitrogen flushed round bottom flask equipped with a stir bar was added pyridine (0.81 mL, 10.0 mmol) and n-pentanol (1.09 mL, 10.0 mmol). The reaction was cooled in an ice bath and triflic anhydride (1.69 mL, 10.0 mmol) was added dropwise. The ice bath was allowed to melt over two hours at which time the entire reaction mixture was filtered over a column of silica gel eluting with dichloromethane. The filtrate was carefully evaporated in vacuo then carried on without further purification(1.11 g, 5.04 mmol).

Workup

  1. customTo a nitrogen flushed round bottom flask equipped with a stir bar
  2. temperatureThe reaction was cooled in an ice bath
  3. customthe entire reaction mixture
  4. filtrationwas filtered over a column of silica gel eluting with dichloromethane
  5. customThe filtrate was carefully evaporated in vacuo
  6. customthen carried on without further purification(1.11 g, 5.04 mmol)

Sources & evidence

ORD record
ord-905ce1a5152a4b5a9c957a0b8bbd92f8
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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