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

HRID 898072Notes

Reaction equation

HRID 898072 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
80 °C

Procedure

5.97 g (55.0 mmol) of chlorotrimethylsilane were added dropwise while stirring at 0° C. to a solution of 5.00 g (49.9 mmol) of acetylacetone and 4.50 g (55.0 mmol) of 1-methylimidazole. The reaction mixture was stirred at 0° C. for a further 1 h and at 80° C. for 5 min to form a liquid biphasic mixture. Removal of the upper phase gave 7.00 g (theory: 8.60 g) of 4-trimethylsilyloxypent-3-en-2-one as a bright yellow, cloudy oil having a purity of 84% (GC).

Workup

  1. customto form a liquid biphasic mixture
  2. customRemoval of the upper phase

Sources & evidence

ORD record
ord-7b179091086c46b29016ef5490b37b8c
Source dataset
uspto-grants-2008_04
Patent number
US07351339B2

Reaction notes

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