4-[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzylidene]tetrahydropyran → 4-(7-Amino-5-methylindan-4-yloxy)-2-(tetrahydropyran-4-yl methyl)phenol

HRID 1766653Notes

Reaction equation

HRID 1766653 reaction equation
C([O:8][C:9]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[C:31]([CH3:32])=[CH:30][C:29]([N+:33]([O-])=O)=[C:28]3[C:24]=2[CH2:25][CH2:26][CH2:27]3)=[CH:18][C:10]=1[CH:11]=[C:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)C1C=CC=CC=1.[H][H]>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:33][C:29]1[CH:30]=[C:31]([CH3:32])[C:23]([O:22][C:19]2[CH:20]=[CH:21][C:9]([OH:8])=[C:10]([CH2:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH:18]=2)=[C:24]2[C:28]=1[CH2:27][CH2:26][CH2:25]2

Participants

6

Reactant 2

HCID 211105754-[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzylidene]tetrahydropyranHCID 178418361HCID 178418361, compound

Product 1

HCID 230311814-(7-Amino-5-methylindan-4-yloxy)-2-(tetrahydropyran-4-yl methyl)phenolYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy) benzylidene]tetrahydropyran (230 mg) was dissolved in ethanol (10 mL) and ethyl acetate (2 mL). After adding 10% Pd/C (50 mg) under ice-cooling, the mixture was stirred at room temperature under an atmospheric pressure of hydrogen for 24 hours. The insoluble material was removed by filtration. The filtrate was evaporated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel (eluent: exane/ethyl acetate) to give the title compound (138 mg).

Workup

  1. temperaturecooling
  2. customThe insoluble material was removed by filtration
  3. customThe filtrate was evaporated under reduced pressure to dryness
  4. customThe residue was purified by column chromatography on silica gel (eluent: exane/ethyl acetate)

Sources & evidence

ORD record
ord-de6cd3345990483bb65b3dad9d721862
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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