Water → 3-Benzyloxy-2-ethyl-6-(5-methyl-7-nitroindan-4-yloxy)phenol

HRID 1766663Notes

Reaction equation

HRID 1766663 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15](=O)[CH3:16])=[C:13]([OH:18])[C:12]([O:19][C:20]2[C:28]([CH3:29])=[CH:27][C:26]([N+:30]([O-:32])=[O:31])=[C:25]3[C:21]=2[CH2:22][CH2:23][CH2:24]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.O>ClCCl>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH3:16])=[C:13]([OH:18])[C:12]([O:19][C:20]2[C:28]([CH3:29])=[CH:27][C:26]([N+:30]([O-:32])=[O:31])=[C:25]3[C:21]=2[CH2:22][CH2:23][CH2:24]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 211105611-[6-Benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone

Product 1

HCID 230311123-Benzyloxy-2-ethyl-6-(5-methyl-7-nitroindan-4-yloxy)phenolYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[6-benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone (1.081 g) in dichloromethane (18 mL) were added triethylsilane (0.955 mL) and trifluoroacetic acid (6 mL). The mixture was stirred at room temperature overnight. Adding water, the reaction mixture was stirred for 30 min and extracted with dichloromethane. The organic layer was washed with 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 (663 mg).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine successively
  3. dry with materialdried 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-b3a9c73692a2444eadff20bf7e7877d9
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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