Hydrochloric Acid → 4-[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzylidene]tetrahydropyran

HRID 1766657Notes

Reaction equation

HRID 1766657 reaction equation
[Cl-].[CH2:2]([O:9][C:10]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[C:45]([CH3:46])=[CH:44][C:43]([N+:47]([O-:49])=[O:48])=[C:42]3[C:38]=2[CH2:39][CH2:40][CH2:41]3)=[CH:32][C:11]=1[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[O:52]1[CH2:57][CH2:56][C:55](=O)[CH2:54][CH2:53]1.Cl>CS(C)=O>[CH2:2]([O:9][C:10]1[CH:35]=[CH:34][C:33]([O:36][C:37]2[C:45]([CH3:46])=[CH:44][C:43]([N+:47]([O-:49])=[O:48])=[C:42]3[C:38]=2[CH2:39][CH2:40][CH2:41]3)=[CH:32][C:11]=1[CH:12]=[C:55]1[CH2:56][CH2:57][O:52][CH2:53][CH2:54]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 21110566[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzyl]triphenylphosphonium chloride

Product 1

HCID 211105754-[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzylidene]tetrahydropyran

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of [2-benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzyl]triphenylphosphonium chloride (559 mg) in dimethylsulfoxide (20 mL) was added sodium hydride (60%, 49 mg) at room temperature, the mixture was stirred for 15 min. After adding tetrahydro-4H-pyran-4-one (0.15 mL), the reaction mixture was stirred at room temperature for 6 hours. After adding dropwise diluted hydrochloric acid to make the mixture acidify fully, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, 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) to give the title compound (230 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 6 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6043ef445ded4f7badcd4be2cb900cc0
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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