Acetone → 13-Ethyl-11-methylen-gon-4-ene

HRID 1446148

Reaction equation

HRID 1446148 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH3:18][C:19]([CH3:21])=O>>[CH2:4]([C@:2]12[CH2:7][C:6](=[CH2:21])[C@@H:5]3[C@@H:19]4[C:21]([CH2:19][CH2:18][C@H:4]3[C@@H:3]1[CH2:7][CH2:6][CH2:12]2)=[CH:3][CH2:2][CH2:12][CH2:18]4)[CH3:5]

Participants

4

Reactant 3

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 8660116013-Ethyl-11-methylen-gon-4-ene

Procedure

1.3 g (3.79 mmoles) of 13-ethyl-11-methylen-17,17-(1,3-propilendioxy)-gon-4-ene (compound XVIIa) were dissolved in acetone (21 ml) under stirring at room temperature. 250 mg of p-toluensulfonic acid monohydrate were added to the solution so obtained and the stirring at room temperature was continued for 17 hours. After this period a saturated solution of sodium bicarbonate (21 ml) was added to the reaction mixture and the organic solvent was evaporated under vacuum. The so obtained aqueous suspension was extracted with dichloromethane (3×30 ml) and the organic extracts dried on sodium sulfate, filtered and evaporated under vacuum to give 0.88 g (3.11 mmoles; yields 82%) of the intermediate 13-ethyl-11-methylen-gon-4-ene (compound XVIII).

Workup

  1. customso obtained
  2. customthe organic solvent was evaporated under vacuum
  3. customThe so obtained aqueous suspension
  4. extractionwas extracted with dichloromethane (3×30 ml)
  5. customthe organic extracts dried on sodium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customto give

Sources & evidence

ORD record
ord-5c829389181347a79fdb2588641be4c0
Source dataset
uspto-grants-2010_02
Patent number
US07667056B2

Linked notes

Loading…