Calcium Chloride → HCID 54200265, compound

HRID 341855Notes

Reaction equation

HRID 341855 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:14]2[CH2:18][CH2:17][C@H:16]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)[S:15]2)[CH:6]=[C:7]([N+:11]([O-])=O)[C:8]=1[O:9][CH3:10].[Cl-].[Cl-].[Ca+2]>C(O)C.O.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:14]2[CH2:18][CH2:17][C@H:16]([C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)[S:15]2)[CH:6]=[C:7]([NH2:11])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 54221761HCID 54221761, compound

Product 1

HCID 54200265HCID 54200265, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

trans-2-(3,4-Dimethoxy-5-nitrophenyl)-5-(3,4,5-trimethoxyphenyl)-tetrahydrothiophene (0.3 g, 0.69 mmole) was suspended in 10 ml of ethanol. To this was added CaCl2 (72.63 mg, 0.65 mmole) in 2 mL water, followed by zinc metal (1.01 g). The suspension was refluxed for 5 hours, filtered, and the residue was washed with ethanol. The combined filtrate was washed with 10% NaHCO3, water and saturated aqueous sodium chloride, dried over MgSO4 and evaporated in vacuo to an oil that was purified by flash column chromatography using 1:1 hexane/ethyl acetate as solvent (30 mg, 10.8%). 1H NMR (CDCl3): 2.10 (m, 2H); 2.57 (m, 2H); 3.81 (s, 3H); 3.83 (s, 3H); 3.87 (s, 3H); 3.89 (s, 6H); 4.80 (m, 2H); 6.45 (d, 1H); 6.51 (d, 1H); 6.70 (s, 2H).

Workup

  1. temperatureThe suspension was refluxed for 5 hours
  2. filtrationfiltered
  3. washthe residue was washed with ethanol
  4. washThe combined filtrate was washed with 10% NaHCO3, water and saturated aqueous sodium chloride
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo to an oil that
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-7838d6c52372467585ecc843685bf25d
Source dataset
uspto-grants-1999_01
Patent number
US05856323

Reaction notes

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