HCID 13826437, compound → HCID 13826439, compound

HRID 1906926Notes

Reaction equation

HRID 1906926 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[CH2:8][CH2:7][C:6](Cl)([Cl:13])[CH:5](Cl)[C:4]=2[C:3]=1[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>COCCOCCOC.[Zn]>[Cl:12][C:10]1[C:9]2[CH2:8][CH2:7][C:6]([Cl:13])=[CH:5][C:4]=2[C:3]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:2]([CH3:1])[CH:11]=1

Participants

4

Reactant 1

HCID 13826437HCID 13826437, compound

Product 1

HCID 13826439HCID 13826439, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8150DiglymeSolvent

Conditions

Temperature
140 °C

Procedure

Activated zinc dust (0.55 g., 8.43 mmoles) was added to a solution of ethyl 3-(2-methyl-5,6,7,8-tetrahydro-4,7,7,8-tetrachloronaphthalen-1-yl)propanoate in dry diglyme (2.5 ml) and heated and stirred in an oil bath rapidly (10 minutes) to about 140° C. at which time the reaction proceeded vigorously and exothermically and refluxed. The reflux subsided in about 1 minute. Heating with an oil bath at 140°-150° C. was continued for 15 minutes Tlc (silica-CH2Cl2) showed reaction complete. The reaction was cooled to room temperature and partitioned between ether (150 ml) and 1N HCl (25 ml). Extract ether successively with 1N HCl, water four times, saturated solution of NaHCl3 ; dried, (MgSO4), filtered and the solvents evaporated to leave 1.99 g of title compound as a gum. Rf =0.61 (silica-CH2Cl2).

Workup

  1. temperatureheated
  2. temperatureexothermically and refluxed
  3. waitThe reflux subsided in about 1 minute
  4. temperatureHeating with an oil bath at 140°-150° C.
  5. waitwas continued for 15 minutes
  6. customreaction complete
  7. temperatureThe reaction was cooled to room temperature
  8. custompartitioned between ether (150 ml) and 1N HCl (25 ml)
  9. dry with materialdried, (MgSO4),
  10. filtrationfiltered
  11. customthe solvents evaporated

Sources & evidence

ORD record
ord-e31a6fa9c8f9466eb07636b2457d0b23
Source dataset
uspto-grants-1987_03
Patent number
US04654363

Reaction notes

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