Ethyl 2-acetyl-3-benzyloxy-6-(5-methyl-7-nitroindan-4-yloxy)benzoate → Ethyl 2-acetyl-3-hydroxy-6-(5-methyl-7-nitroindan-4-yloxy)benzoate
Reaction equation
[C:1]([C:4]1[C:14]([O:15]CC2C=CC=CC=2)=[CH:13][CH:12]=[C:11]([O:23][C:24]2[C:32]([CH3:33])=[CH:31][C:30]([N+:34]([O-:36])=[O:35])=[C:29]3[C:25]=2[CH2:26][CH2:27][CH2:28]3)[C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O.O.CSC>[C:1]([C:4]1[C:14]([OH:15])=[CH:13][CH:12]=[C:11]([O:23][C:24]2[C:32]([CH3:33])=[CH:31][C:30]([N+:34]([O-:36])=[O:35])=[C:29]3[C:25]=2[CH2:26][CH2:27][CH2:28]3)[C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]Participants
3
Procedure
Ethyl 2-acetyl-3-benzyloxy-6-(5-methyl-7-nitroindan-4-yloxy)benzoate (314 mg) was dissolved in trifluoroacetic acid/water/dimethylsulfide (95/5/10) (3 mL). The mixture was stood overnight at room temperature and evaporated under reduced pressure to dryness. Adding water, the residue was extracted with ethyl acetate. 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 purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1−3/1) to give the title compound (217 mg).
Workup
- customevaporated under reduced pressure to dryness
- extractionAdding water, the residue was extracted with ethyl acetate
- washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine successively
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1−3/1)
Sources & evidence
- ORD record
- ord-95855b6b84294681b4c11b1402f17f10
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07230031B2
Reaction notes
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