Methanol → HCID 14411904, compound

HRID 1759040Notes

Reaction equation

HRID 1759040 reaction equation
[CH:1]([Mg]Br)=[CH2:2].C[O:6][C:7]1[CH2:11][CH2:10][C:9](=O)[C:8]=1[CH3:13].CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH:8]([C:9]1[CH2:10][CH2:11][C:7](=[O:6])[C:1]=1[CH3:2])=[CH2:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 11018872HCID 11018872, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 14411904HCID 14411904, compoundYield 322.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A one-liter, three-necked flask equipped with a mechanical stirrer, reflux condenser, dropping funnel and nitrogen inlet was flamed out under nitrogen. After 65.6 g (0.05 mole) vinyl magnesium bromide in 500 ml THF was transferred to the reaction flask, 23.3 g (0.18 mole) of 3-methoxy-2-methyl-2-cyclopentenone 7 in 100 ml of dry THF was then added dropwise over a period of several hours. For the reasons supra, methanol with p-toluenesulfonic acid, may be preferred for larger quantity production. The mixture was cooled and then stirred into a four-liter beaker containing 1 kg of cracked ice. After adjustment to pH 3 with concentrated HCl, the reaction mixture was extracted with CHCl3. After washing the combined chloroform extracts with water, the solvent was removed under reduced pressure to give 19.7 g of a yellow liquid. This material was distilled (55°-56° C. at 0.1 mm) to give a 60% yield:nmr (CDCl3) δ7.2-5.2 (m,3, --CH=CH2) and 1.8 (s,3, --CH3).

Workup

  1. customA one-liter, three-necked flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperaturewas flamed out under nitrogen
  4. additionwas then added dropwise over a period of several hours
  5. temperatureThe mixture was cooled
  6. extractionAfter adjustment to pH 3 with concentrated HCl, the reaction mixture was extracted with CHCl3
  7. washAfter washing the combined chloroform
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4e2056b682174b1bae02d48de75db15b
Source dataset
uspto-grants-1982_07
Patent number
US04338466

Reaction notes

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