Propargyl bromide → HCID 10988319, compound

HRID 520373Notes

Reaction equation

HRID 520373 reaction equation
[H-].[Na+].[CH2:3]([CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:4]=[CH2:5].Br[CH2:18][C:19]#[CH:20]>CN(C=O)C.CCOCC>[CH2:3]([C:6]([CH2:20][C:19]#[CH:18])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:4]=[CH2:5]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 74900Diethyl allylmalonate

Product 1

HCID 10988319HCID 10988319, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

NaH (60%, 0.480 g) was added to a cold (0° C.) solution of diethyl 2-allylmalonate (2.002 g) in DMF (10 mL) and the mixture was allowed to warm to rt over 30 min. Then a solution of 3-bromoprop-1-yne (1.487 g) in DMF (3 mL) was added dropwise at 0° C. and the mixture was allowed to warm to rt and stirred at rt overnight. The reaction mixture was diluted with ether and then quenched with sat. NH4Cl, washed with water, brine and dried (Na2SO4). The crude product was purified by silica gel FCC (1:1 DCM-hexane) to afford diethyl 2-allyl-2-(prop-2-ynyl)malonate as a clear oil.

Workup

  1. temperatureto warm to rt
  2. customquenched with sat. NH4Cl
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customThe crude product was purified by silica gel FCC (1:1 DCM-hexane)

Sources & evidence

ORD record
ord-334d8c57c1cd497f980340039500de54
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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