Diisopropylethylamine → (E)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-butenoic Acid Ethyl Ester

Participants

Reaction Steps

DIEA (2.75 mL, 16.6 mmol) and LiCl (5.54 g, 129 mmol) were added to a solution of tert-butyldimethylsilyloxy acetaldehyde (3.22 g, 18.5 mmol) and diethylmethylphosphonoacetate (4.66 g, 22.2 mmol) in CH3CN (40 mL) and the mixture was stirred at rt for 24 hrs. The mixture was quenched with water (50 mL) and extracted with EtOAc (50 mL). The organic layer was dried over MgSO4 and concentrated. The residue was purified via flash chromatography eluting with 25% EtOAc/heptane to give the title compound as a colorless oil (3.27 g, 72% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 6.91 (dt, J=15.42, 3.49 Hz, 1H) 6.01 (dt, J=15.61, 2.27 Hz, 1H) 4.25 (dd, J=3.27, 2.27 Hz, 2H) 4.12 (q, J=7.22 Hz, 2H) 1.21 (t, J=7.18 Hz, 3H) 0.84 (s, 9H) 0.00 (s, 6H).

Provenance & Evidence