Cesium carbonate → HCID 55269048, compound

HRID 1755058Notes

Reaction equation

HRID 1755058 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].Br[CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CCOCC.[Cu](I)I.[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+].[Cl-].C12([N+]3C=CN(C45CC6CC(CC(C6)C4)C5)C=3)CC3CC(CC(C3)C1)C2>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH3:15]

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 127321-HexyneHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 55269048HCID 55269048, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-CatalystHCID 83717Copper iodideCatalystHCID 27349151,3-Di(tricyclo[3.3.1.1~3,7~]decan-1-yl)-1H-imidazol-3-ium chlorideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
45 °C

Procedure

1-Hexyne (43 μl, 0.38 mmol) and ethyl 4-bromobutyrate (40 μl, 0.28 mmol) were added to a suspension of 1,3-bis(1-adamantyl)imidazolium chloride (5.2 mg, 0.014 mmol), copper iodide (4.1 mg, 0.022 mmol), allylpalladium(II) chloride dimer (2.6 mg, 0.071 mmol) and cesium carbonate (127 mg, 0.390 mmol) in anhydrous ether (0.37 ml)-anhydrous DMF (0.185 ml) at room temperature in a nitrogen stream, and the mixture was stirred at 45° C. for 17 hours. The reaction mixture was extracted with pentane. The insoluble matter was removed by filtration, and the filtrate was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ether=50/1) to give dec-5-ynoic acid ethyl ester (40 mg, 73%).

Workup

  1. extractionThe reaction mixture was extracted with pentane
  2. customThe insoluble matter was removed by filtration
  3. concentrationthe filtrate was then concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/ether=50/1)

Sources & evidence

ORD record
ord-a8f6768d3ff54bb2a2fb74cd297f04c9
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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