Trifluoromethanesulfonic anhydride → HCID 10517725, compound

HRID 1020890Notes

Reaction equation

HRID 1020890 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 357781Ethyl 6-hydroxyhexanoate

Product 1

HCID 10517725HCID 10517725, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To the suspension of poly(4-methylpyridine) (2.24 g, 2 eq) in newly dried dichloromethane (25 mL ) at 0° C. was added trifluoromethanesulfonic anhydride (5 g, 1 eq) drop wise over 30 mins. Ethyl 6-hydroxyhexanoate (2.76 g, 0.95 eq) was then added in drop wise via a syringe. The mixture was stirred at 0° C. for 4 hrs and the polymer was filtered off by a frit. The solvent was evaporated under reduced pressure (without heating) and the crude product was subjected to a short silica gel pad with 1:4 (v/v) diethyl ether/hexane as the eluent solvent. The solvent was evaporated (without heating) and the product was used directly in the following step. (3.9 g, 75% yield based on ethyl 6-hydroxyhexanoate.) See FIG. 10.

Workup

  1. filtrationthe polymer was filtered off by a frit
  2. customThe solvent was evaporated under reduced pressure (without heating)
  3. customThe solvent was evaporated
  4. temperature(without heating)

Sources & evidence

ORD record
ord-1decd84120c040069954e7c809639666
Source dataset
uspto-grants-2014_05
Patent number
US08716491B2

Reaction notes

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