Chlorotrimethylsilane → 2-acetyltrop-2-ene

Temperature

-100 °C

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 (1.4M, 17.07 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); 1H NMR (CDCl3) δ6.7 (bt, 1H), 2.3 (s, NCH3), 2.2 (s, C(≡O)CH3).

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

ORD record

ord-2f175e7851544622b48024d1d9cce427

Source dataset

uspto-grants-1994_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05306718