Dimethylformamide → HCID 57091011, compound

HRID 1975632Notes

Reaction equation

HRID 1975632 reaction equation
CN(C)C=O.[O-]CCCC.[K+].[CH3:12][C:13](=[CH:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH:21]([CH3:24])[C:20]1([CH3:26])[CH3:25])[C:14](=[O:16])[CH3:15]>C(O)(=O)C>[CH3:12][CH:13]([CH:17]=[CH:18][CH:19]1[CH2:23][CH2:22][CH:21]([CH3:24])[C:20]1([CH3:25])[CH3:26])[C:14](=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 23699084Potassium butoxideHCID 537486543-Methyl-5-(2,2,3-trimethylcyclopentyl)pent-3-en-2-one

Product 1

HCID 57091011HCID 57091011, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a mixture of 100 ml of N,N-dimethylformamide and 13 g (0.18 mole) of powdered potassium butoxide, maintained at 20°-30° C. are added slowly within 1 hour 25 g (0.12 mole) of 3-methyl-5-(2,2,3-trimethyl-cyclopent-1-yl)-pent-3-ene-2-one. The resultant mixture is stirred at ambient temperature for 4 hours (reaction is monitored by GC) and is cooled to 10° C. The reaction mixture is drained out of the reaction flask into a beaker containing 20 ml of glacial acetic acid and 50 ml of ice water which are being stirred by means of a magnetic stirrer. The mixture is stirred for 5-10 minutes and is then transferred to a separatory funnel. This mixture is extracted with three 50 ml portions of toluene. The toluene extracts are combined and washed with three 50 ml portions of 10% sodium bicarbonate solution and one 100 ml portion of saturated sodium chloride solution. The solvent is removed by rotary evaporation and the oil is fractionally distilled to yield 5.2 g of 3-methyl-5-(2,2,3-trimethyl-cyclopent-1-yl)-pent-4-en-2-one (mixtures of isomers).

Workup

  1. temperaturemaintained at 20°-30° C.
  2. custom(reaction is monitored by GC)
  3. stirringThe mixture is stirred for 5-10 minutes
  4. customis then transferred to a separatory funnel
  5. extractionThis mixture is extracted with three 50 ml portions of toluene
  6. washwashed with three 50 ml portions of 10% sodium bicarbonate solution and one 100 ml portion of saturated sodium chloride solution
  7. customThe solvent is removed by rotary evaporation
  8. distillationthe oil is fractionally distilled

Sources & evidence

ORD record
ord-b02f817d823a4b768953d60ad2d77175
Source dataset
uspto-grants-1994_02
Patent number
US05288701

Reaction notes

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