Hydrochloric Acid → HCID 57444528, compound

HRID 860414Notes

Reaction equation

HRID 860414 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(=O)([O-])[O-].[Cs+].[Cs+].Cl>C(#N)C.CS(C)=O.C(OCC)(=O)C>[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

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 31261Acetylacetone2×HCID 122490Ethyl 7-bromoheptanoate

Product 1

HCID 57444528HCID 57444528, compoundYield 45.8%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

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 partitoned 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 (5.5 g) as an oil.

Workup

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

Sources & evidence

ORD record
ord-eb41946ed6f74613a6cdaf25ed56d5c2
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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