Triethylamine → 7-Methoxybenzofuran-3-yl trifluoromethanesulfonate

HRID 495414Notes

Reaction equation

HRID 495414 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9](=O)[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[S:20]([O:27]S(C(F)(F)F)(=O)=O)([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([O:27][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 223269427-Methoxy-2,3-dihydro-1-benzofuran-2-one

Product 1

HCID 208271337-Methoxybenzofuran-3-yl trifluoromethanesulfonateYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution (−20° C.) of 3.3 g (20 mmol) 7-methoxy-benzofuranone in 30 mL methylene chloride was added 8.3 mL (6.0 mmol) of triethylamine. To the cold mixture, a solution of 8.5 g (30 mmol) of triflic anhydride in 20 ml of methylene chloride was added dropwise. The temperature was kept at −20° C. or 1 hour. The reaction was then quenched with 100 mL of saturated aqueous sodium bicarbonate aand extracted with methylene chloride (2×150 mL). The combined organic extracts were dried over magnesium sulfate and concentrated in vacuum to give 5.6 g of the desired product. MS (ES) m/z (relative intensity): 265 (M+H, 100);

Workup

  1. customThe reaction was then quenched with 100 mL of saturated aqueous sodium bicarbonate
  2. extractionextracted with methylene chloride (2×150 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-d9916e5142e04c089d9d4cf70beb9d79
Source dataset
uspto-grants-2005_09
Patent number
US06939877B2

Reaction notes

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