Potassium Carbonate → HCID 57444528, compound

HRID 2250556Notes

Reaction equation

HRID 2250556 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CS(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[C:4]([CH:3]([C:2](=[O:7])[CH3:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:6])[CH3:5]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 31261Acetylacetone2×HCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 57444528HCID 57444528, compoundYield 458.4%

Reagents, catalysts & solvents 3

HCID 10796Cesium carbonateCatalystHCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of pentane-2,4-dione (5.0 g), ethyl 7-bromoheptanoate (11.1 g), potassium carbonate (13.8 g), and cesium carbonate (1.63 g) in a mixture of acetonitrile (150 ml) and dimethylsulfoxide (30 ml) was stirred at 20° C. overnight, then pentane-2,4-dione (5 g) was added. After stirring at 20° C. overnight, the mixture was partitioned between ethyl acetate and 0.5N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5) to give ethyl 8-acetyl-9-oxodecanoate (55 g) as an oil.

Workup

  1. stirringAfter stirring at 20° C. overnight
  2. customthe mixture was partitioned between ethyl acetate and 0.5N hydrochloric acid
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5)

Sources & evidence

ORD record
ord-13930eba857945e7a6c292e105afb909
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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