ETHYL 3-OXO-4-(TRIPHENYLPHOSPHORANYLIDENE)BUTYRATE

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of {3-(ethoxycarbonyl)-2-oxopropyl}triphenyl phosphonium chloride (21.34 g, 500 mmol) in water (450 mL) was added to a solution of sodium carbonate (3.1 g, 25.0 mmol) in 10 min (Note: A white precipitate was obtained immediately after the addition). This reaction mixture was stirred at room temperature overnight. The precipitate that obtained was filtered off through a sintered funnel. The precipitate was dissolved in dichloromethane (100 mL), dried over sodium sulfate and concentrated to yield a white solid 18.13 g (93%). This material was dried over phosphorus pentoxide overnight. 1H NMR (CDCl3) δ 1.26 (t, 3H), 3.34 (s, 2H), 3.76-3.84 (d, 1H) 4.19 (m, 2H) and 7.48-7.68 (m, 15H, PhH). A white precipitate was obtained immediately after the addition) The precipitate that obtained was filtered off through a sintered funnel The precipitate was dissolved in dichloromethane (100 mL) dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of {3-(ethoxycarbonyl)-2-oxopropyl}triphenyl phosphonium chloride (21.34 g, 500 mmol) in water (450 mL) was added to a solution of sodium carbonate (3.1 g, 25.0 mmol) in 10 min (Note: A white precipitate was obtained immediately after the addition). This reaction mixture was stirred at room temperature overnight. The precipitate that obtained was filtered off through a sintered funnel. The precipitate was dissolved in dichloromethane (100 mL), dried over sodium sulfate and concentrated to yield a white solid 18.13 g (93%). This material was dried over phosphorus pentoxide overnight. 1H NMR (CDCl3) δ1.26 (t, 3H), 3.34 (s, 2H), 3.76-3.84 (d, 1H) 4.19 (m, 2H) and 7.48-7.68 (m, 15H, PhH). A white precipitate was obtained immediately after the addition) The precipitate that obtained was filtered off through a sintered funnel The precipitate was dissolved in dichloromethane (100 mL) dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of {3-(ethoxycarbonyl)-2-oxopropyl}triphenyl phosphonium chloride (21.34 g, 500 mmol) in water (450 mL) was added to a solution of sodium carbonate (3.1 g, 25.0 mmol) in 10 min (Note: A white precipitate was obtained immediately after the addition). This reaction mixture was stirred at room temperature overnight. The precipitate that obtained was filtered off through a sintered funnel. The precipitate was dissolved in dichloromethane (100 mL), dried over sodium sulfate and concentrated to yield a white solid 18.13 g (93%). This material was dried over phosphorus pentoxide overnight. 1H NMR (CDCl3) δ 1.26 (t, 3H), 3.34 (s, 2H), 3.76-3.84 (d, 1H) 4.19 (m, 2H) and 7.48-7.68 (m, 15H, PhH). A white precipitate was obtained immediately after the addition) The precipitate that obtained was filtered off through a sintered funnel The precipitate was dissolved in dichloromethane (100 mL) dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of {3-(ethoxycarbonyl)-2-oxopropyl}triphenyl phosphonium chloride (21.34 g, 500 mmol) in water (450 mL) was added to a solution of sodium carbonate (3.1 g, 25.0 mmol) in 10 min (Note: A white precipitate was obtained immediately after the addition). This reaction mixture was stirred at room temperature overnight. The precipitate that obtained was filtered off through a sintered funnel. The precipitate was dissolved in dichloromethane (100 mL), dried over sodium sulfate and concentrated to yield a white solid 18.13 g (93%). This material was dried over phosphorus pentoxide overnight. 1H NMR (CDCl3) δ 1.26 (t, 3H), 3.34 (s, 2H), 3.76-3.84 (d, 1H) 4.19 (m, 2H) and 7.48-7.68 (m, 15H, PhH). A white precipitate was obtained immediately after the addition) The precipitate that obtained was filtered off through a sintered funnel The precipitate was dissolved in dichloromethane (100 mL) dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: triphenylphosphine (30.0 g, 114.3 mmol) is added, at ambient temperature, to a solution of commercial ethyl 4-chloro-3-oxobutanoate (18.81 g, 114.3 mmol) in 200 mL of anhydrous THF. The reaction medium is taken to reflux for 18 h before being concentrated under vacuum. The oil obtained is taken up in distilled water then washed with ether. The aqueous phase is then basified by a saturated aqueous solution of NaHCO3 (up to pH 8). After extraction with AcOEt, the organic phases are combined, dried over MgSO4, filtered then concentrated under vacuum. Purification is carried out by recrystallization from ether in order to produce, after filtration and drying, compound 5′-2 (14.96 g, 38.0 mmol, 34%) in the form of a slightly yellow solid. to reflux for 18 h before being concentrated under vacuum The oil obtained then washed with ether After extraction with AcOEt dried over MgSO4 filtered then concentrated under vacuum Purification is carried out by recrystallization from ether in order to produce after filtration drying

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (3-ethoxycarbonyl-2-oxopropylidene)triphenylphosphorane (5.0 g, 12.8 mmol) in tetrahydrofuran (THF, 50 ml) were added sodium hydride (60% dispersion in oil, 1.03 g, 25.6 mmol) and then pentanal (1.10 g, 12.8 mmol) followed by stirring. After addition of water (three drops), the mixture was heated at 45° C. for 1 hour. The reaction mixture was treated with dilute hydrochloric acid and extracted with ether. The organic layer was washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride, dried (MgSO4), and concentrated to dryness. The resulting residue was purified by column chromatography on silica gel. The column was eluted with dichloromethane-hexane (1:1 to 3:2) to give 1.02 g (40.0%) of the title compound as an oil. The 1H-NMR spectrum indicates that the product is a mixture of keto/enol isomers. extracted with ether The organic layer was washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride dried (MgSO4) concentrated to dryness The resulting residue was purified by column chromatography on silica gel The column was eluted with dichloromethane-hexane (1:1 to 3:2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of {3-(ethoxycarbonyl)-2-oxopropyl}triphenyl phosphonium chloride (21.34 g, 500 mmol) in water (450 mL) was added to a solution of sodium carbonate (3.1 g, 25.0 mmol) in 10 min (Note: A white precipitate was obtained immediately after the addition). This reaction mixture was stirred at room temperature overnight. The precipitate that obtained was filtered off through a sintered funnel. The precipitate was dissolved in dichloromethane (100 mL), dried over sodium sulfate and concentrated to yield a white solid 18.13 g (93%). This material was dried over phosphorus pentoxide overnight. 1H NMR (CDCl3) δ1.26 (t, 3H), 3.34 (s, 2H), 3.76-3.84 (d, 1H) 4.19 (m, 2H) and 7.48-7.68 (m, 15H, PhH). A white precipitate was obtained immediately after the addition) The precipitate that obtained was filtered off through a sintered funnel The precipitate was dissolved in dichloromethane (100 mL) dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of {3-(ethoxycarbonyl)-2-oxopropyl}triphenyl phosphonium chloride (21.34 g, 500 mmol) in water (450 mL) was added to a solution of sodium carbonate (3.1 g, 25.0 mmol) in 10 min (Note: A white precipitate was obtained immediately after the addition). This reaction mixture was stirred at room temperature overnight. The precipitate that obtained was filtered off through a sintered funnel. The precipitate was dissolved in dichloromethane (100 mL), dried over sodium sulfate and concentrated to yield a white solid 18.13 g (93%). This material was dried over phosphorus pentoxide overnight. 1H NMR (CDCl3) δ 1.26 (t, 3H), 3.34 (s, 2H), 3.76-3.84 (d, 1H) 4.19 (m, 2H) and 7.48-7.68 (m, 15H, PhH). A white precipitate was obtained immediately after the addition) The precipitate that obtained was filtered off through a sintered funnel The precipitate was dissolved in dichloromethane (100 mL) dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of {3-(ethoxycarbonyl)-2-oxopropyl}triphenyl phosphonium chloride (21.34 g, 500 mmol) in water (450 mL) was added to a solution of sodium carbonate (3.1 g, 25.0 mmol) in 10 min (Note: A white precipitate was obtained immediately after the addition). This reaction mixture was stirred at room temperature overnight. The precipitate that obtained was filtered off through a sintered funnel. The precipitate was dissolved in dichloromethane (100 mL), dried over sodium sulfate and concentrated to yield a white solid 18.13 g (93%). This material was dried over phosphorus pentoxide overnight. 1H NMR (CDCl3) δ1.26 (t, 3H), 3.34 (s, 2H), 3.76-3.84 (d, 1H) 4.19 (m, 2H) and 7.48-7.68 (m, 15H, PhH). A white precipitate was obtained immediately after the addition) The precipitate that obtained was filtered off through a sintered funnel The precipitate was dissolved in dichloromethane (100 mL) dried over sodium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of {3-(ethoxycarbonyl)-2-oxopropyl}triphenyl phosphonium chloride (21.34 g, 500 mmol) in water (450 mL) was added to a solution of sodium carbonate (3.1 g, 25.0 mmol) in 10 min (Note: A white precipitate was obtained immediately after the addition). This reaction mixture was stirred at room temperature overnight. The precipitate that obtained was filtered off through a sintered funnel. The precipitate was dissolved in dichloromethane (100 mL), dried over sodium sulfate and concentrated to yield a white solid 18.13 g (93%). This material was dried over phosphorus pentoxide overnight. 1H NMR (CDCl3) δ 1.26 (t, 3H), 3.34 (s, 2H), 3.76-3.84 (d, 1H) 4.19 (m, 2H) and 7.48-7.68 (m, 15H, PhH). A white precipitate was obtained immediately after the addition) The precipitate that obtained was filtered off through a sintered funnel The precipitate was dissolved in dichloromethane (100 mL) dried over sodium sulfate concentrated