Hydrochloric Acid → 3-{2-[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]vinyl}furan

HRID 1766652Notes

Reaction equation

HRID 1766652 reaction equation
[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[O:7][CH:6]=[CH:5][CH:4]=1.[CH3:27][C:28](C)([O-])C.[K+].[CH2:33]([O:40][C:41]1[CH:48]=[CH:47][C:46]([O:49][C:50]2[C:58]([CH3:59])=[CH:57][C:56]([N+:60]([O-:62])=[O:61])=[C:55]3[C:51]=2[CH2:52][CH2:53][CH2:54]3)=[CH:45][C:42]=1C=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl>O1CCCC1>[CH2:33]([O:40][C:41]1[CH:48]=[CH:47][C:46]([O:49][C:50]2[C:58]([CH3:59])=[CH:57][C:56]([N+:60]([O-:62])=[O:61])=[C:55]3[C:51]=2[CH2:52][CH2:53][CH2:54]3)=[CH:45][C:42]=1[CH:27]=[CH:28][C:5]1[CH:4]=[CH:3][O:7][CH:6]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11418806Furfuryltriphenylphosphonium bromideHCID 23031138HCID 23031138, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 694253463-{2-[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)phenyl]vinyl}furanYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of furfuryltriphenylphosphonium bromide (377 mg) in tetrahydrofuran (30 mL) was added potassium tert-butoxide (136 mg) at room temperature, and the mixture was stirred for 15 min. After adding 2-benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzaldehyde (377 mg), the 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 (306 mg).

Workup

  1. stirringthe 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 solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3a268b5b5f91487391d9266c57426c06
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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