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

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).

1. customThe mixture was quenched with water (50 mL)
2. extractionextracted with EtOAc (50 mL)
3. dry with materialThe organic layer was dried over MgSO4
4. concentrationconcentrated
5. customThe residue was purified via flash chromatography
6. washeluting with 25% EtOAc/heptane

ORD record

ord-444ecef71af54f71bedfc9a2081b4281

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040547B2