Water → 1-Trimethylsilyloxy-4-isopropenyl-1-cyclohexene

HRID 1419802Notes

Reaction equation

HRID 1419802 reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[O:3][C:4]1[CH2:9][CH2:8][CH:7]([C:10](=O)[CH3:11])[CH2:6][CH:5]=1.O.[CH3:16]COCC>>[CH3:1][Si:2]([CH3:14])([CH3:13])[O:3][C:4]1[CH2:9][CH2:8][CH:7]([C:10]([CH3:16])=[CH2:11])[CH2:6][CH:5]=1

Participants

4

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 139399121-{4-[(Trimethylsilyl)oxy]cyclohex-3-en-1-yl}ethan-1-one

Product 1

HCID 543729751-Trimethylsilyloxy-4-isopropenyl-1-cyclohexene

Procedure

From 23.5 g (0.066 mol) of methyltriphenylphosphonium bromide and 6.9 g (0.061 mol) of potassium tert-butylate, in 80 ml of ether at room temperature, the ylide was formed. To this solution were added dropwise at from 20° to 30° C. 10.0 g (0.047 mol) of 1-trimethylsilyloxy-4-acetyl-1-cyclohexene (Org. Synth. Coll. Vol. VI, 445) dissolved in 20 ml of ether. The mixture was stirred at room temperature for 3 hours. Water was then added, and extraction was carried out with ether. A spatula tip of hydroquinone was added to the combined ether phases, which were then dried and concentrated. The residue was extracted by stirring with heptane and the combined heptane phases were concentrated. 8.0 g (81% of theory) were obtained of a colorless oil which was reacted further without purification.

Workup

  1. additionTo this solution were added dropwise at from 20° to 30° C
  2. extractionextraction
  3. additionA spatula tip of hydroquinone was added to the combined ether phases, which
  4. customwere then dried
  5. concentrationconcentrated
  6. extractionThe residue was extracted
  7. stirringby stirring with heptane
  8. concentrationthe combined heptane phases were concentrated
  9. custom8.0 g (81% of theory) were obtained of a colorless oil which
  10. customwas reacted further without purification

Sources & evidence

ORD record
ord-fbac8f2f5d80498dbc487c690ad64e76
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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