Tetrahydrofuran → HCID 86689308, compound

HRID 1852493Notes

Reaction equation

HRID 1852493 reaction equation
O1CCCC1.[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([NH:20][C:21]2[C:22]([NH2:31])=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:17]=[CH:18][CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:32](Cl)(=[O:37])[CH2:33][C:34](Cl)=[O:35]>CO>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([N:20]2[C:34](=[O:35])[CH2:33][C:32](=[O:37])[NH:31][C:22]3[C:23]4[CH2:24][CH2:25][CH2:26][CH2:27][C:28]=4[CH:29]=[CH:30][C:21]2=3)[CH:17]=[CH:18][CH:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 74269Propanedioyl dichlorideHCID 86689306HCID 86689306, compound

Product 1

HCID 86689308HCID 86689308, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an anhydrous tetrahydrofuran (15 mL) solution of N2-(3-benzyloxyphenyl)-5,6,7,8-tetrahydronaphthalene-1,2-diamine (151 mg, 0.44 mmol) was added malonyl chloride (50 μL, 0.53 mmol) while stirring in ice-bath. The mixture was stirred at room temperature for 3 hours. To the mixture was added methanol (5 mL) while stirring in ice-bath. The mixture was stirred under cooling in ice-bath for 1 hour, and at room temperature for 1 hour. The solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to give the titled compound as yellow oil (58 mg, yield 32%).

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. stirringwhile stirring in ice-bath
  3. stirringThe mixture was stirred
  4. temperatureunder cooling in ice-bath for 1 hour
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-c21b7794d0474aee844baad2250e04df
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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