Triethylamine → 1-Oxo-2,3-dihydro-1H-inden-4-yl trifluoromethanesulfonate

HRID 1615034Notes

Reaction equation

HRID 1615034 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].O[C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][CH2:20][C:21]2=[O:26].CCN(CC)CC>C(Cl)Cl>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][CH2:20][C:21]2=[O:26])(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 218380021-Oxo-2,3-dihydro-1H-inden-4-yl trifluoromethanesulfonateYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triflic anhydride (152 g, 0.54 mol) was added dropwise to solution 80 g of compound 86 and 60 g of NEt3 in 1 L CH2Cl2 at 0° C. The resulting mixture was refluxed for 2 h, cooled to room temperature, filtered, washed with water (0.5 L), aqueous citric acid (50 g/0.5 L), brine (0.5 L), dried on Na2SO4, and evaporated to give about 100 g (67%) of compound 87 as dark liquid.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. filtrationfiltered
  3. washwashed with water (0.5 L), aqueous citric acid (50 g/0.5 L), brine (0.5 L)
  4. customdried on Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-84966184106f4239a90b4ca1e0fae548
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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