ethyl (2E)-3-cyclopropylacrylate synthesis
- Product Name:ethyl (2E)-3-cyclopropylacrylate
- CAS Number:21014-26-6
- Molecular formula:C8H12O2
- Molecular Weight:140.18
Yield:21014-26-6 97%
Reaction Conditions:
Stage #1: diethoxyphosphoryl-acetic acid ethyl esterwith sodium hydride in tetrahydrofuran at 0 - 20;
Stage #2: Cyclopropanecarboxaldehyde in tetrahydrofuran at 20; for 2 h;
Steps:
12.A preparation of ethyl 3-cyclopropylacrylate
Ethyl 2-(diethoxyphosphoryl)acetate (39.83 mL, 200.7 mmol) was dissolved in THF (300 ml) and cooled to 0 °C. Sodium hydride (8.029 g, 200.7 mmol) was added portion-wise and the reaction warmed to ambient temperature. After 1 hour cyclopropane carboxaldehyde (10.00 mL, 133.8 mmol) was added drop-wise and the reaction allowed to stir at ambient temperature for 2 hours. The reaction mixture was diluted with saturated aqueous NaHC03 and EtOAc. The combined organic layers were washed with brine, dried over MgS04 and concentrated under reduced pressure to afford the crude material. The crude material was purified by a silica gel plug eluting with 75% hexanes/CH2Cl2 to afford 18.5g (97%) of the desired product as a colorless oil. The product was determined to be a 97:3 mixture of the E:Z isomers by 1H NMR.
References:
WO2013/55645,2013,A1 Location in patent:Paragraph 00391
