1-Methylimidazole → 3-Penten-2-one, 4-[(trimethylsilyl)oxy]-

HRID 500047Notes

Reaction equation

HRID 500047 reaction equation
Cl[Si:2]([CH3:5])([CH3:4])[CH3:3].[C:6]([CH2:9][C:10](=[O:12])[CH3:11])(=[O:8])[CH3:7].CN1C=CN=C1>>[CH3:3][Si:2]([CH3:5])([CH3:4])[O:12][C:10]([CH3:11])=[CH:9][C:6](=[O:8])[CH3:7]

Participants

4

Reactant 3

HCID 13901-MethylimidazoleHCID 6397ChlorotrimethylsilaneHCID 31261Acetylacetone

Product 1

HCID 1146323-Penten-2-one, 4-[(trimethylsilyl)oxy]-Yield 81.4%

Conditions

Temperature
0 °C

Procedure

5.97 g (55.0 mmol) of chlorotrimethylsilane were added dropwise to a solution of 5.00 g (49.9 mmol) of acetylacetone and 4.50 g (55.0 mmol) of 1-methylimidazole while stirring at 0° C. The reaction mixture was stirred for another 1 hour at 0° C. and for 5 minutes at 80° C., resulting in the formation of a liquid two-phase mixture. The upper phase was separated off to give 7.00 g (theory: 8.60 g) of 4-trimethylsilyloxypent-3-en-2-one as a light-yellow, turbid oil having a purity of 84% (GC).

Workup

  1. stirringThe reaction mixture was stirred for another 1 hour at 0° C. and for 5 minutes at 80° C.
  2. customresulting in the formation of a liquid two-phase mixture
  3. customThe upper phase was separated off

Sources & evidence

ORD record
ord-75f7dc428fb44361b530bd9f2f94074d
Source dataset
uspto-grants-2010_08
Patent number
US07767852B2

Reaction notes

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