Water → HCID 58136322, compound

HRID 877165Notes

Reaction equation

HRID 877165 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[C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][C:20]([CH3:30])([C:26]([O:28][CH3:29])=[O:27])[CH2:21]2.O>N1C=CC=CC=1>[CH3:30][C:20]1([C:26]([O:28][CH3:29])=[O:27])[CH2:21][C:22]2[C:18](=[CH:17][CH:25]=[CH:24][C:23]=2[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 67749Trifluoromethanesulfonic anhydrideHCID 58136741HCID 58136741, compound

Product 1

HCID 58136322HCID 58136322, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At −15° C., 1.5 ml (8.7 mmol) of trifluoromethanesulfonic anhydride were slowly added dropwise to a solution of 897 mg (4.35 mmol) of methyl 4-hydroxy-2-methyl-2,3-dihydro-1H-indene-2-carboxylate in 20 ml of pyridine. After warming to room temperature, the reaction mixture was stirred for another 2 h. 20 ml of water were then added and, after phase separation, the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent was removed to dryness under reduced pressure. The crude product obtained was purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 1100 mg (3.25 mmol, 75% of theory) of a colorless oil.

Workup

  1. customafter phase separation
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed to dryness under reduced pressure

Sources & evidence

ORD record
ord-77b3a46741b14b97adbeaddd91a46316
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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