2-propenoic acid, 3-cyclopropyl-2-Methyl-, ethyl ester synthesis
- Product Name:2-propenoic acid, 3-cyclopropyl-2-Methyl-, ethyl ester
- CAS Number:21014-30-2
- Molecular formula:C9H14O2
- Molecular Weight:154.21
Yield:21014-30-2 73.3%
Reaction Conditions:
Stage #1: diethoxyphosphoryl-acetic acid ethyl esterwith n-butyllithium in tetrahydrofuran at -78; for 1 h;
Stage #2: Cyclopropanecarboxaldehyde in tetrahydrofuran at -78; for 1 h;
Steps:
A ethyl (E)-3-cyclopropyl-2-methylprop-2-enoate
A solution of ethyl 2- diethoxyphosphorylpropanoate (2.38 g, 10.0 mmol) in THF (30 mL) was cooled to -78 °C and n- BuLi (2.4 N, 4.58 mL) was added dropwise and stirred at -78 °C for 1 h. Then cyclopropanecarbaldehyde (0.70 g, 10 mmol) was added dropwise and stirred at -78 °C for 1 h. The mixture was quenched with saturated aqueous NH4ci and extracted with EtOAc, washed with brine, dried over anhydrous Na2SC>4, and concentrated to dryness to give the title compound as a yellow liquid (1.13 g, 73.3% yield). MS (ESI): mass calcd. for C9H14O2, 154.1 ; m/z found, 155.1 [M+H]+.
References:
WO2017/100668,2017,A1 Location in patent:Page/Page column 168
