Reaktion #664909

Reaktionsgleichung

DIEA

LiCl

tert-butyldimethylsilyloxy acetaldehyde

diethylmethylphosphonoacetate

→

title compound

Ausbeute 80.6%

ethyl (2E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-2-enoate

Ausbeute 80.6%

Lösungsmittel

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was quenched with water (50 mL)
2. 2
   Extraktionextracted with EtOAc (50 mL)
3. 3
   TrocknenThe organic layer was dried over MgSO4
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified via flash chromatography
6. 6
   Wascheneluting with 25% EtOAc/heptane

Vorschrift

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).

Quelle