Chlorotrimethylsilane → 2-acetyltrop-2-ene

HRID 374763Notes

Reaction equation

HRID 374763 reaction equation
[C@@H:1]12[N:8]([CH3:9])[C@@H:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]=[C:2]2[C:10]([O:12]CC)=O.[Si](Cl)(C)(C)[CH3:16].[Li]C>C1COCC1>[C:10]([C:2]1[C@@H:1]2[N:8]([CH3:9])[C@H:5]([CH2:4][CH:3]=1)[CH2:6][CH2:7]2)(=[O:12])[CH3:16]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 25222744Anhydroecgonine ethyl esterHCID 178418348HCID 178418348, compound

Product 1

HCID 108774782-acetyltrop-2-eneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture, of ethyl trop-2-ene-2-carboxylate (3.43 g, 0.019 mol) and Me3SiCl (10.32 g, 0.095 mol) in THF (70 mL) cooled to -100° C., MeLi (1.4 M, 7.07 mL, 0.0239 mol) was added dropwise. After warming up to room temperature, the reaction mixture was stirred for 16 hours. Excess Me3SiCl and THF was evaporated off and the resulting residue was stirred with EtOH (6 mL) followed by water (6 mL). The mixture was then made acidic (6N HCl) and extracted with ether. The aqueous layer was made basic (solid K2CO3) and extracted with chloroform, dried (K2CO3) and concentrated to give 3.14 g (81%) of 2-acetyltrop-2-ene as an oil: IR (neat) 1670 (COCH3);

Workup

  1. customExcess Me3SiCl and THF was evaporated off
  2. stirringthe resulting residue was stirred with EtOH (6 mL)
  3. extractionmade acidic (6N HCl) and extracted with ether
  4. extractionextracted with chloroform
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-548a090ab15246c99fad9c59786c8bb3
Source dataset
uspto-grants-1996_01
Patent number
US05482938

Reaction notes

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