Propargyl bromide → 2,4-Pentanedione, 3-(2-propynyl)-

HRID 1775761Notes

Reaction equation

HRID 1775761 reaction equation
[CH2:1](Br)[C:2]#[CH:3].C([O-])([O-])=O.[K+].[K+].[CH3:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15]>CC(C)=O>[CH2:3]([CH:13]([C:12](=[O:17])[CH3:11])[C:14](=[O:16])[CH3:15])[C:2]#[CH:1]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 31261Acetylacetone

Product 1

HCID 51488022,4-Pentanedione, 3-(2-propynyl)-Yield 80.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of propargyl bromide (0.32 g, 2.70 mmol), K2CO3 (2.22 g, 16.10 mmol), and 2,4-pentane-dione (1.34 g, 13.40 mmol) in acetone (30 mL) was stirred for 24 hrs at 60° C. After filtration and removal of solvent under reduced pressure, the crude residue was purified by flash chromatography (hexane) to give 22 as colorless liquid (0.30 g, 69%). 1HNMR (400 MHz, CDCl3) δ 2.03-2.04 (t, J=5.28 Hz, 1H), 2.22 (s, 3H), 2.25 (s, 3H), 2.68-2.71 (m, 2H), 3.84-3.87 (t, J=15.08 Hz, 1H); 13CNMR (100 MHz, CDCl3) δ 14.45, 29.33, 29.41, 68.70, 70.79, 86.13, 202.18, 202.63.

Workup

  1. filtrationAfter filtration and removal of solvent under reduced pressure
  2. customthe crude residue was purified by flash chromatography (hexane)

Sources & evidence

ORD record
ord-eb3e7e6cd91d41d8a3c400a1d2540872
Source dataset
uspto-grants-2016_02
Patent number
US09260473B2

Reaction notes

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