Methanol → HCID 21883344, compound

HRID 722421Notes

Reaction equation

HRID 722421 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=[O:13])[CH2:7][CH2:6]2.N1CC[CH2:16][CH2:15]1.CO.C(I)C>C1(C)C=CC=CC=1>[CH2:15]([CH:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH2:6][CH2:7][C:8]1=[O:13])[CH3:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 6340IodoethaneHCID 31268PyrrolidineHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 21883344HCID 21883344, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6-methoxy-2-tetralone (120.55 grams, 0.684 mol) and pyrrolidine (61 mL, 0.685 mol) in toluene (1.7 L) was heated to reflux using a Dean-Stark trap apparatus for 3 hours. After removal of the azeotroped water, the reaction mixture was cooled to room temperature and concentrated to a solid. To this solid was added methanol (1.2 L) and ethyl iodide (121 mL, 1.51 mol). The resulting solution was heated at reflux overnight and then concentrated under vacuum to remove methanol. A solution of acetic acid (120 mL), sodium acetate (120 g) in water (240 mL) was added to the residue and the resultant mixture was heated at reflux for 2 hours. After cooling, the mixture was extracted several times with diethyl ether. The combined organic layers were washed twice with aqueous 1M HCl, twice with aqueous 1M NaOH and once with brine. After drying over magnesium sulfate, the solvent was evaporated to afford the title compound as an oil, 121.8 grams. Mass spectrum: m/e 204.

Workup

  1. temperatureto reflux
  2. customfor 3 hours
  3. customAfter removal of the azeotroped water
  4. concentrationconcentrated to a solid
  5. temperatureThe resulting solution was heated
  6. temperatureat reflux overnight
  7. concentrationconcentrated under vacuum
  8. customto remove methanol
  9. additionA solution of acetic acid (120 mL), sodium acetate (120 g) in water (240 mL) was added to the residue
  10. temperaturethe resultant mixture was heated
  11. temperatureat reflux for 2 hours
  12. temperatureAfter cooling
  13. extractionthe mixture was extracted several times with diethyl ether
  14. washThe combined organic layers were washed twice with aqueous 1M HCl, twice with aqueous 1M NaOH and once with brine
  15. dry with materialAfter drying over magnesium sulfate
  16. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bc02f92710d442438606c681c45966a7
Source dataset
uspto-grants-2006_11
Patent number
US07138406B2

Reaction notes

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