Hydrochloric Acid → HCID 15430948, compound

HRID 725771Notes

Reaction equation

HRID 725771 reaction equation
[C:1](=[O:10])([O:6][CH2:7][CH:8]=[CH2:9])OCC=C.[H-].[Na+].[CH3:13][C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15].Cl>C(OCC)C.O.O1CCCC1>[CH:16]1([C:14]([CH2:13][C:1]([O:6][CH2:7][CH:8]=[CH2:9])=[O:10])=[O:15])[CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 13004Cyclopropyl methyl ketoneHCID 24758Sodium hydrideHCID 84764Carbonic acid, di-2-propen-1-yl ester

Product 1

HCID 15430948HCID 15430948, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Preparation of the β-ketoester. To a round bottom flask equipped with an addition funnel and cold water condenser was added, 21.3 grams (0.15 mol.) of diallyl carbonate and 50 mL of tetrahydrofuran and the mixture was stirred. Next, sodium hydride, 8.4 grams (0.21 mol.), was added portion-wise. To the reaction mixture was added, 12.6 grams (0.15 mol.) of cyclopropyl methyl ketone (dissolved in 25 mL of tetrabydrofuran) via the addition funnel. The mixture was heated to relux and heated for an additional 1 hour. Subsequently, the mixture was allowed to cool and the solvent was stripped. Next, cold water (50 mL) and 1N hydrochloric acid (50 mL) were added. The reaction mixture was transferred to a separatory funnel and diethyl ether was added. The organic layer was dried over MgSO4 and stripped under vacuum to yield the β-ketoester, carboallyloxymethyl cyclopropyl ketone. ##STR15## (B) Preparation of aryl β-triketone. To a round bottom flask was added 23.6 grams (0.14 mol.) of the β-ketoester, 16 grams (0.14 mol.) of magnesium ethoxide and 100 mL of tetrahydrofuran. The reaction mixture was then refluxed for 2 hours and the solvent stripped to insure complete removal of the ethanol by-product. The flask was then recharged with 100 mL of tetrahydrofuran and 29.3 grams (0.14 mol.) of the aryl acid chloride. The solution was refluxed for several hours, after which the mixture was stripped under vacuum, extracted with diethyl ether and washed with water. The 46.4 grams of β-triketone product, trifluoromethylbenzoylcarboallyloxy-methyl cyclopropyl ketone were confirmed by infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS).

Workup

  1. customTo a round bottom flask equipped with an addition funnel and cold water condenser
  2. additionwas added
  3. additionTo the reaction mixture was added
  4. temperatureThe mixture was heated
  5. temperatureheated for an additional 1 hour
  6. temperatureto cool
  7. customThe reaction mixture was transferred to a separatory funnel
  8. dry with materialThe organic layer was dried over MgSO4

Sources & evidence

ORD record
ord-b4ca4d8f329d41b98bb5ba0f585f0440
Source dataset
uspto-grants-1998_01
Patent number
US05707930

Reaction notes

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