HCID 15790541, compound → HCID 15279914, compound

HRID 22188Notes

Reaction equation

HRID 22188 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:10](=[O:12])[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH2:8]2

Participants

3

Reactant 1

HCID 15790541HCID 15790541, compound

Product 1

HCID 15279914HCID 15279914, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

The crude product from Step A was combined with 50 ml of thionyl chloride and then heated at reflux for 2 hours. Thionyl chloride was removed by concentration at reduced pressure and then the mixture was concentrated several times from carbon tetrachloride. The residue was combined with 200 ml of dichloroethane, cooled under nitrogen to 0° C., and 24.5 g of aluminum trichloride was then added. After stirring overnight the reaction was poured onto a mixture of ice in 1N hydrochloric acid, extracted three times with ether and chromatographed on silica gel (10% ethyl acetate/hexane) to afford 18.6 g of a yellow oily solid. 1H NMR (CDCl3) δ 3.20 (dd, 1H), 3.68 (dd, 1H), 3.90 (dd, 1H), 6.9-7.6 (m), 7.75 (d, 1H) .

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThionyl chloride was removed by concentration at reduced pressure
  4. concentrationthe mixture was concentrated several times from carbon tetrachloride
  5. addition24.5 g of aluminum trichloride was then added
  6. additionwas poured onto a mixture of ice in 1N hydrochloric acid
  7. extractionextracted three times with ether
  8. customchromatographed on silica gel (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b25578a38644477e9ab9dcdeead3cd00
Source dataset
uspto-grants-1995_06
Patent number
US05428027

Reaction notes

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