Réaction #2643

Équation de réaction

sodium bicarbonate

tert-butyl trichloroacetimidate

boron trifluoride diethyl etherate

4-hydroxy-2-cyclopentenone

→

title compound

Rendement 40.0%

4-tert-butoxy-cyclopent-2-enone

Rendement 40.0%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températureto warm to room temperature
2. 2
   workup.STIRRINGstirred for 22 hours
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate is concentrated under vacuum
5. 5
   Autrethe residue is purified by chromatography (silica gel, 39 g, 20% ethyl acetate/hexane, 600 mL)

Mode opératoire

A solution of 4-hydroxy-2-cyclopentenone (1.15 g, 11.7 mmol) in methylene chloride is cooled to 3° C. and treated sequentially with tert-butyl trichloroacetimidate (4.2 mL, 23.7 mmol) and boron trifluoride diethyl etherate (0.15 mL). The reaction mixture is stirred at 3-10° C. for 2 hours and then allowed to warm to room temperature and stirred for 22 hours. The reaction mixture is then treated with sodium bicarbonate (250 mg) and filtered. The filtrate is concentrated under vacuum and the residue is purified by chromatography (silica gel, 39 g, 20% ethyl acetate/hexane, 600 mL) to provide the title compound (355 mg, 40%) as a yellow oil; 1H NMR (CDCl3)δ7.44 (dd, 1H, J=18 Hz), 6.2 (d, 1H, J=5.4 Hz), 4.8 (m, 1H), 2.68 (dd, 1H, J=5.8, 18 Hz), 2.25 (d, 1H, J=18 Hz), 1.27 (s, 9H); IR (neat) νmax 2976, 2936, 1721, 1368, 1352, 1188, 1103, 1161 cm-1 ; MS (CI) m/e (% relative intensity) 155 (M+H+, 22), 99 (100).

Source