Diethyl Ether → 1,3-Cyclopentanedione, 2,2-dimethyl-

HRID 2357015Notes

Reaction equation

HRID 2357015 reaction equation
[OH-].[K+].[CH3:3][CH:4]1[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10].CI.[CH2:13](OCC)C>O.O1CCOCC1.CCCCCC>[CH3:3][C:4]1([CH3:13])[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 130052-Methyl-1,3-cyclopentanedioneHCID 14797Potassium Hydroxide

Product 1

HCID 197631,3-Cyclopentanedione, 2,2-dimethyl-Yield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of potassium hydroxide (15.0 g, 0.27 mol) in water (40 ml) was added to a stirred solution of 2-methylcyclopentane-1,3-dione 1 (25.0 g, 0.22 mol) in 1,4-dioxane (120 ml) at room temperature. Methyl iodide (100 g, 0.70 mol) was then added and the resulting solution was heated under reflux for 15 hours. The mixture was then cooled to room temperature and extracted with ethyl acetate (4×160 ml). The combined extracts were then dried over MgSO4 and evaporated in vacuo. Flash chromatography (SiO2, 60% diethyl ether in hexane) gave the dione 2 (18.0 g, 0.14 mol, 64%) as a white solid; δH (300 MHz, CDCl3) 2.80 (4H, s, CH2CH2), 1.16 (3H, s, CH3), 1.15 (3H, s, CH3); δC (75.5 MHz, CDCl3) 216.3 (s), 52.6 (s), 34.5 (t), 20.2 (q).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 15 hours
  3. extractionextracted with ethyl acetate (4×160 ml)
  4. dry with materialThe combined extracts were then dried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4946216c4eb24c5988f2df1e919acda7
Source dataset
uspto-grants-2010_07
Patent number
US07759399B2

Reaction notes

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