Water → HCID 21110568, compound

HRID 1766690Notes

Reaction equation

HRID 1766690 reaction equation
[F:1][C:2]([F:32])([F:31])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[C:19]3[C:15]=2[CH2:16][CH2:17][CH2:18]3)=[C:9]([OH:27])[C:8]=1[C:28](=O)[CH3:29])(=[O:5])=[O:4].C([SiH](CC)CC)C.FC(F)(F)C(O)=O.O>ClCCl>[F:31][C:2]([F:1])([F:32])[S:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[C:19]3[C:15]=2[CH2:16][CH2:17][CH2:18]3)=[C:9]([OH:27])[C:8]=1[CH2:28][CH3:29])(=[O:4])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 23031246HCID 23031246, compound

Product 1

HCID 21110568HCID 21110568, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-acetyl-3-hydroxy-4-(5-methyl-7-nitroindan-4-yloxy)phenyl trifluoromethanesulfonate (477 mg) in dichloromethane (5 mL) were added triethylsilane (0.960 mL) and trifluoroacetic acid (5 mL), and the mixture was stirred at room temperature overnight. Adding water, the reaction mixture was stirred for 1 hour and extracted with dichloromethane. The organic layer was washed with water, a saturated aqueous solution of sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was crystallized from dichloromethane and hexane to give the title compound (274 mg).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and brine successively, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was crystallized from dichloromethane and hexane

Sources & evidence

ORD record
ord-204170e4f92f45fabb2281bf31ec78dd
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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