Benzene → HCID 57166467, compound

HRID 1728981Notes

Reaction equation

HRID 1728981 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH:9]=[CH:8][CH2:7][C@H:6]1[C:11]([OH:13])=O)=[O:4].S(Cl)(Cl)=O.[CH:18]1C=CC=CC=1>>[C:11]([C@@H:6]1[CH2:7][CH:8]=[CH:9][CH2:10][C@@H:5]1[C:3]([O:2][CH3:1])=[O:4])(=[O:13])[CH3:18]

Participants

4

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 53259071-Methyl (1S,2R)-4-cyclohexene-1,2-dicarboxylate

Product 1

HCID 57166467HCID 57166467, compound

Conditions

Temperature
-5 °C

Procedure

25 g of (1R, 2S)-2-methoxycarbonylcyclohex-4-ene-1-carboxylic acid and 40 ml of thionyl chloride were dissolved in 200 ml of dry benzene, and the mixture was refluxed for two hours. The solvent was distilled off under a reduced pressure, and to the residue was added ml of dried tetrahydrofuran. Further, 1.29 g of copper (I) iodide was added to the solution, which was cooled to -5° C, 182 ml of tetrahydrofuran solution of methylmagnesium bromide (0.82M) was added dropwise to the solution over a period of 1.5 hours. The solution was further stirred for one hour at the same temperature, and then 1N-hydrochloric acid was added. After the organic layer was separated, the water layer was extracted with ether. The organic layer was successively washed with 5% sodium thiosulfate solution, saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate: hexane=15:85) to be purified, and thus 18.27 g of the titled compound was obtained.

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. distillationThe solvent was distilled off under a reduced pressure
  3. additionto the residue was added ml of dried tetrahydrofuran
  4. additionFurther, 1.29 g of copper (I) iodide was added to the solution, which
  5. addition182 ml of tetrahydrofuran solution of methylmagnesium bromide (0.82M) was added dropwise to the solution over a period of 1.5 hours
  6. addition1N-hydrochloric acid was added
  7. customAfter the organic layer was separated
  8. extractionthe water layer was extracted with ether
  9. washThe organic layer was successively washed with 5% sodium thiosulfate solution, saturated sodium bicarbonate solution and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated
  12. customto be purified

Sources & evidence

ORD record
ord-c70cb42b009845ae904911ac1848f3d3
Source dataset
uspto-grants-1994_07
Patent number
US05329042

Reaction notes

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