Pyridine → HCID 86622665, compound

HRID 2195591Notes

Reaction equation

HRID 2195591 reaction equation
[CH3:1][C:2]12[CH2:12][CH:6]3[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([C:13]4(O)[CH:18]=[CH:17][CH:16]=[CH:15][CH2:14]4)([CH2:5]3)[CH2:3]1)[CH2:9]2.N1C=CC=CC=1.[F:26][C:27]([F:40])([F:39])[S:28]([O:31]S(C(F)(F)F)(=O)=O)(=[O:30])=[O:29].[Cl-].[Na+]>C(OCC)(=O)C>[CH3:11][C:8]12[CH2:7][CH:6]3[CH2:12][C:2]([CH3:1])([CH2:3][C:4]([C:13]4[CH:14]=[CH:15][C:16]([O:31][S:28]([C:27]([F:40])([F:39])[F:26])(=[O:30])=[O:29])=[CH:17][CH:18]=4)([CH2:5]3)[CH2:10]1)[CH2:9]2

Participants

6

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 67749Trifluoromethanesulfonic anhydrideHCID 86622664HCID 86622664, compound

Product 1

HCID 86622665HCID 86622665, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-15 °C

Procedure

Into a 100 ml four-necked flask equipped with a thermometer, an inlet for nitrogen gas and a stirrer, 4.0 g (0.0157 moles) of 4-(1-(3,5-dimethyladamantyl)phenol obtained above and 20 ml of pyridine were placed. A stream of nitrogen gas was introduced into the flask, and a solution was prepared under stirring. The obtained solution was cooled at −15° C. in an ice/methanol bath. Using a dropping funnel, trifluoromethanesulfonic acid anhydride was added dropwise. After the addition was completed, the obtained mixture was stirred at the room temperature for 2 hours. To the reaction fluid, 100 ml of ethyl acetate and 100 ml of a saturated aqueous solution of sodium chloride were added, and the obtained mixture was transferred to a separation funnel. The layer of ethyl acetate was taken out and washed twice with 100 ml of a saturated aqueous solution of sodium chloride. Then, ethyl acetate was removed by distillation under a reduced pressure using a rotary evaporator, and 5.4 g of 1-(1-(3,5-dimethyladamantyl)-4-trifluoromethane-sulfonyloxybenzene was obtained (the yield: 88%).

Workup

  1. additionA stream of nitrogen gas was introduced into the flask
  2. customa solution was prepared
  3. additionAfter the addition
  4. stirringthe obtained mixture was stirred at the room temperature for 2 hours
  5. customthe obtained mixture was transferred to a separation funnel
  6. washwashed twice with 100 ml of a saturated aqueous solution of sodium chloride
  7. customThen, ethyl acetate was removed by distillation under a reduced pressure
  8. customa rotary evaporator, and 5.4 g of 1-(1-(3,5-dimethyladamantyl)-4-trifluoromethane-sulfonyloxybenzene
  9. customwas obtained (the yield: 88%)

Sources & evidence

ORD record
ord-25048aec6f6d40429930d97d7b7ee6ce
Source dataset
uspto-grants-2012_12
Patent number
US08337982B2

Reaction notes

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